(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL

(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL - Names and Identifiers

Name	(-)-2,3-O-isopropylidene-1,1,4,4-tetra-phenyl-D-threitol
Synonyms	(+)-TADDOL (+)-Taddol Bishydroxydiphenylmethyldimethyldioxolane (+)-trans-A,A-(2,2-dimethyl-1,3-dioxolane-4,5-D (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL (-)-2,3-O-isopropylidene-1,1,4,4-tetra-phenyl-D-threitol (4S,5S)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-DIOXOLANE (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2,2-DIMETHYL-1,3-DIOXOLANE (4S,5S)-2,2-Dimethyl-α,α,α',α'-tetraphenyldioxolane-4,5-dimethanol [(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethanol) (2S,3S)-(+)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE (2S,3S)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-1,2,3,4-BUTANETETROL (2S,3S)-(+)-1,1,4,4-TETRAPHENYL-2,3-(2-PROPYLIDENEDIOXY)-BUTANE-1,4-DIOL (4S,5S)-2,2-Dimethyl-alpha,alpha,alpha,alpha-tetraphenyldioxolane-4,5-dimethanol (4S,5S)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRAPHENYLDIOXOLANE-4,5-DIMETHANOL
CAS	93379-49-8
InChI	InChI=1/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m0/s1
InChIKey	RNSJHECWLNVNFE-LOYHVIPDSA-N

(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL - Physico-chemical Properties

Molecular Formula	C31H30O4
Molar Mass	466.57
Density	1.200±0.06 g/cm3(Predicted)
Melting Point	193-196°C(lit.)
Boling Point	633.2±50.0 °C(Predicted)
Specific Rotation(α)	-62.6 º (c=1 in chloroform)
Flash Point	336.718°C
Vapor Presure	0mmHg at 25°C
Appearance	powder to crystal
Color	White to Almost white
BRN	4724097
pKa	12.28±0.29(Predicted)
Storage Condition	Inert atmosphere,Room Temperature
Refractive Index	1.615
MDL	MFCD00010079
Use	Ligands for enantioselective Lewis acid-mediated Diels-Alder reactions, etc.

(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL - Risk and Safety

Hazard Symbols	Xn - Harmful
Risk Codes	R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing.
WGK Germany	3
HS Code	29329990

(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL - Introduction

(-)-2,3-O-isopropylidene-1,1,4,4-tetra-phenyl-D-threitol ((-)-2,3-O-isopropylmethylene -1,1, 4,4-tetraphenyl-D-triethanol), often abbreviated as DIPT.

Nature:
DIPT is a solid substance, the appearance of white crystals, it has a chiral (oblique) molecular structure. Its chemical formula is C34H32O2 and its molecular weight is 480.62. DIPT has a high melting point and boiling point, it is soluble in some organic solvents (such as methanol, chloroform, dichloromethane, etc.), but insoluble in water.

Use:
DIPT is an organic compound, which is often used as a chiral inducer and a synthetic intermediate for chiral molecules in organic synthesis. It can be used in the preparation of chiral drugs, chiral ligands and chiral catalysts. Because of its high chiral induction effect, DIPT is widely used in the field of drug development and chemical research.

Method:
The preparation method of DIPT is more complicated and is generally achieved by multi-step synthesis. Here is a possible synthetic route:

1. obtaining methylphenol by synthesizing phenol and methylmagnesium bromide;
2. reaction of methylphenol with dibenzyl peroxide to synthesize dimethylcyclopentanone;
3. reacting dimethyl cyclopentanone with tert-butyl hydroperoxide to obtain the peroxide product of dimethyl cyclopentanone;
4. DIPT was prepared by reacting the peroxide product dimethyl cyclopentanone with benzyl alcohol.

Safety Information:
Since DIPT is a highly chiral organic compound, care should be taken to prevent potentially harmful effects on the human body when using and handling it. Wear appropriate protective equipment such as gloves, goggles and laboratory clothing during laboratory operations. In addition, DIPT should be stored properly to avoid contact with oxidants and high-temperature ignition sources to prevent the risk of fire and explosion. If contact with skin or inhalation, should be timely cleaning, and medical treatment. For specific safety information, refer to the safety data sheet of the relevant chemical.

Last Update：2024-04-09 21:04:16