106445-04-9

Basic information

• Product Name: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol
• Synonyms: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol
• CAS NO: 106445-04-9
• Molecular Weight: 424.61
• Mol File: 106445-04-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol(106445-04-9)
• EPA Substance Registry System: 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol(106445-04-9)

Safety Data

• Hazardous Substances Data: 106445-04-9(Hazardous Substances Data)

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 

Downstream Products

• 106445-05-0 3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose 
• 888954-88-9 methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester 
• 881894-81-1 2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-yl)ethanol 
• 888954-89-0 [2-azido-2-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethoxy]-tert-butyl dimethylsilane 
• 888954-87-8 [1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl]carbamic acid benzyl ester 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 1311161-45-1 6-deoxy-6-phthalimido-5-O-(tert-butyldimethylsilyl)-3-O-benzyl-1,2-O-isopropylidene-D-glucofuranose 
• 106445-06-1 methyl 3-O-benzyl-5-C-tert-butyldimethylsilyloxymethyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-(Z)-enofuranosyluronate 
• 106445-06-1 (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid methyl ester 
• 106499-05-2 (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol 
• 94393-42-7 (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol 
• 106445-11-8 (R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione 
• 94393-43-8 (2R,3R)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol 
• 94393-44-9 (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol 

Relevant articles and documents

An unexpected migration of O-silyl group under Mitsunobu reaction conditions

A 1,4 O→O silyl migration followed by nucleophilic substitution with phthalimide was observed under Mitsunobu reaction conditions. This one step secondary alcohol protection and primary alcohol substitution with N-nucleophiles was extended to a variety of

Modular synthesis of heparin oligosaccharides

A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).