112330-11-7

Basic information

• Product Name: (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside
• Synonyms: (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside
• CAS NO: 112330-11-7
• Molecular Weight: 692.804
• Mol File: 112330-11-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside(112330-11-7)
• EPA Substance Registry System: (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside(112330-11-7)

Safety Data

• Hazardous Substances Data: 112330-11-7(Hazardous Substances Data)

Upstream product

• 58931-11-6 (C₄H₉)3SnOCH₂C₇H₅O₅(CH₃)4 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 84207-56-7 6-O-<(3'R,4'R,5'R)-5'-hydroxy-3',4',6'-tribenzyloxyhex-1'(Z)-enyl>-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 244282-14-2 (3aR,5R,5aS,8aS,8bR)-5-[1-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-1-methyl-ethoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 244282-10-8 phenyl 3,4,6-tri-O-benzyl-2-O-(2-propenyl)-1-thio-β-D-glucopyranoside 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 301645-88-5 methyl 2-O-(1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)-2-iodopropyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 358351-82-3 2-O-(1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)-2-iodopropyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 
• 793672-62-5 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-β-D-glucopyranoside 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 793672-55-6 p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 793672-57-8 4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 301645-86-3 methyl 2-O-(prop-1-enyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 153947-47-8 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant articles and documents

Protecting Group Dependence of Stereochemical Outcome of Glycosylation of 2-O-(Thiophen-2-yl)methyl Ether Protected Glycosyl Donors

A series of glycosyl donors possessing a (thiophen-2-yl)methyl ether protecting group at position 2 were synthesised and the effect of the protecting group pattern of other hydroxyls on the stereochemical outcome of glycosylation was investigated. Studies revealed optimal α-selectivity for glycosylation using a fully armed tri-benzylated donor, whilst other protecting group patterns were significantly less effective. Low-temperature NMR studies of both fully armed and fully disarmed donors revealed the intermediacy of cyclised sulfonium ion intermediates. Reaction conditions were developed which allowed removal of the (thiophen-2-yl)methyl ether protecting group either selectively, or together with benzyl ethers. Glycosyl donors with a 2-O-thiophenylmethyl ether protecting group undergo six-membered ring NGP, as demonstrated by low-T NMR studies, but the stereochemical outcome of glycosylation is highly dependent on other protecting groups.

Stereoselective glycosylations using oxathiane spiroketal glycosyl donors

Novel oxathiane spiroketal donors have been synthesised and activated via an umpolung S-arylation strategy using 1,3,5-trimethoxybenzene and 1,3-dimethoxybenzene. The comparative reactivity of the resulting 2,4,6-trimethoxyphenyl (TMP)- and 2,4-dimethoxyp

Stereoselective glycosylation using oxathiane glycosyl donors

A bicyclic glycosyl donor is activated as an arylsulfonium ion and used to synthesise α-glycosides with high stereoselectivity.