81086-90-0

Basic information

• Product Name: methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside
• Synonyms: methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside
• CAS NO: 81086-90-0
• Molecular Weight: 464.558
• Mol File: 81086-90-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside(81086-90-0)
• EPA Substance Registry System: methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside(81086-90-0)

Safety Data

• Hazardous Substances Data: 81086-90-0(Hazardous Substances Data)

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 67-56-1 methanol 
• 100-44-7 benzyl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 81120-51-6 1,2-O-((1RS)-1-ethoxyethylidene)-β-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 3254-15-7 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose 
• 81928-95-2 (2S,3R,4S,5S,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran 
• 101758-39-8 (4aR,6S,7R,8S,8aS)-7,8-Bis-allyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 88819-25-4 2,3-di-O-allyl-α-D-galactopyranoside 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 

Downstream Products

• 58341-63-2 methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 129948-14-7 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 20672-69-9 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 93636-31-8 Methyl 2,3-di-O-acetyl-4,6-di-O-benzyl-α-D-mannopyranoside 
• 77117-44-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 64694-18-4 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant articles and documents

Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses

- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Immunomodulatory α-Galactoglycosphingolipids: Synthesis of a 2′-O-Methyl-α-Gal-GSL and Evaluation of Its Immunostimulating Capacity

The total synthesis of 1-2-docosanoylamino-O-(2-O-methyl-α -D-galactopyranosyl)-1,3,4-octadecanetriol (2), a 2′-methoxy analog of the immunostimulating α-galactoglycosphingolipid 1, is reported. Stereoselective α-glycosylation of the azido precursor of sp

Triisobutylaluminium and dusobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins

To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then induces the regioselectivity of the de-O-alkylation by coordinating preferentially to one of the oxygen atoms of the selected pair.

Trimethylaluminium promoted rearrangements of unsaturated sugars into cyclohexanes

Trimethylaluminium induces a stereoselective rearrangement of unsaturated glycosides into polyfunctionalised cyclohexanic rings containing a tertiary alcohol and retaining the anomeric group. In contrast with the previously used triisobutylaluminium, no de-O-benzylation reaction was observed.

Allyl protecting group mediated intramolecular aglycon delivery: Optimisation of mixed acetal formation and mechanistic investigation

An efficient protocol for the formation of α-iodo mixed acetals, the first step of allyl-mediated IAD, by reaction of allyl-derived enol ethers and alcohols, using I2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, i

Allyl protecting group mediated intramolecular aglycon delivery (IAD) of glycosyl fluorides

Stereospecific 1,2-cis-glycosylation of 2-O-allyl protected glucosyl and mannosyl fluorides can be achieved via a sequence of allyl isomerization, N-iodosuccinimide mediated tethering, and intramolecular aglycon delivery (IAD). Fluoride is advantageous as

N-Iodosuccinimide-mediated intramolecular aglycon delivery

Enol ethers may be accessed via Tebbe methylenation of either 2-O acetates or para-methoxybenzoates. N-Iodosuccinimide may then be employed to achieve both tethering and thioglycoside activation allowing the stereoselective synthesis of α-glucosides and β-mannosides, either in a one or two step procedure.

Stereospecific synthesis of 1,2-cis glycosides by allyl-mediated intramolecular aglycon delivery. 2.The use of glycosyl fluorides.

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-allyl-protected glucosyl and mannosyl fluorides via a sequence of allyl isomerization, N-iodosuccinimide-mediated tethering, and intramolecular aglycon delivery (IAD) is reported. The use of