53735-98-1

Basic information

• Product Name: 1,2:5,6-di-O-isopropylidene-D-glucitol
• Synonyms: 1,2:5,6-di-O-isopropylidene-D-glucitol;1-O,2-O:5-O,6-O-Bis(1-methylethylidene)-D-glucitol;1-O,2-O:5-O,6-O-Diisopropylidene-D-glucitol;Einecs 258-736-5
• CAS NO: 53735-98-1
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.29948
• EINECS: 258-736-5
• Mol File: 53735-98-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 382°C at 760 mmHg
• Flash Point: 184.8°C
• Appearance: /
• Density: 1.175g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Refractive Index: 1.476
• CAS DataBase Reference: 1,2:5,6-di-O-isopropylidene-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-di-O-isopropylidene-D-glucitol(53735-98-1)
• EPA Substance Registry System: 1,2:5,6-di-O-isopropylidene-D-glucitol(53735-98-1)

Safety Data

• Hazardous Substances Data: 53735-98-1(Hazardous Substances Data)

Usage

Chemical compound

Yes

Purpose

Used as a protecting group in organic synthesis

Derived from

D-glucitol and isopropylidene

Function

Protects hydroxyl groups during chemical reactions, preventing unwanted side reactions

Applications

a. Production of pharmaceuticals
b. Manufacturing of various chemicals and substances

Industry uses

a. Food industry as a sweetener
b. Food industry as a bulking agent

Safety

Generally considered safe for consumption

Role

Crucial in organic synthesis

Commercial uses

Diverse applications across different sectors

InChI:InChI=1/C12H22O6/c1-11(2)15-5-7(17-11)9(13)10(14)8-6-16-12(3,4)18-8/h7-10,13-14H,5-6H2,1-4H3

Upstream product

• 50-70-4 D-sorbitol 
• 71240-80-7 C₂₆H₃₀O₈ 
• 77-76-9 2,2-dimethoxy-propane 
• 4306-35-8 1,2-isopropylidene-D-glucitol 
• 69-65-8 mannitol 
• 71696-36-1 3,4-di-O-acetyl-1,2:5,6-di-O-isopropylidene-D-glucitol 
• 50-70-4 D-glucitol 
• 67-64-1 acetone 
• 4306-35-8 1,2-O-isopropylidene-D-glucitol 

Downstream Products

• 71240-80-7 O³,O⁴-dibenzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-glucitol 
• 56-82-6 Glyceraldehyde 
• 5736-03-8 (d,l) isopropylidene glyceraldehyde 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 652-67-5 Isosorbide 
• 95058-92-7 (erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate 

Relevant articles and documents

Novel preparation method for gemcitabine hydrochloride

The invention discloses a preparation method for gemcitabine hydrochloride. The preparation method comprises the steps: carrying out condensation, cracking and addition on D-mannitol serving as an initial raw material, and protecting hydroxyl by TESC1 to prepare an intermediate; and after carrying out condensation on the intermediate and cytosine under the catalysis of chiral phosphoric acid, carrying out salification to prepare gemcitabine hydrochloride. The preparation method has the advantages that the reaction steps are reduced, and the cost is reduced. Due to the use of the chiral phosphoric acid, the proportion of a required beta structure is greatly increased, the ratio of beta to alpha can reach 9:1, and the yield is increased. The chiral phosphoric acid belongs to an organic acidand is recyclable, little to environment pollution and particularly suitable for industrial production of gemcitabine hydrochloride.

Free-Radical Chemistry of Imines

Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group.When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated.However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines.Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered.Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.

SOME ASPECTS OF THE ISOPROPYLIDENATION OF D-GLUCITOL UNDER NEUTRAL CONDITIONS

Isopropylidenation of D-glucitol (1) under neutral conditions, by treatment with 2,2-dimethoxypropane in 1,2-dimethoxyethane, has been studied.An improved procedure for the isolation of 1,2:5,6-di-O-isopropylidene-D-glucitol, the main equilibrium product, by direct crystallisation or via the 3,4-dibenzoate is described.Some aspects of the reaction are discussed and compared with results obtained previously from the isopropylidenation of 1 in the presence of zinc chloride.