127243-54-3

Basic information

• Product Name: METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE
• Synonyms: METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE
• CAS NO: 127243-54-3
• Molecular Weight: 478.585
• Mol File: 127243-54-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE(127243-54-3)
• EPA Substance Registry System: METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE(127243-54-3)

Safety Data

• Hazardous Substances Data: 127243-54-3(Hazardous Substances Data)

Upstream product

• 139070-96-5 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside 
• 127214-51-1 methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 127924-45-2 (2R,3S,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-3-trimethylsilanylethynyl-tetrahydro-pyran-3-ol 
• 127924-41-8 (2R,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-dihydro-pyran-3-one 
• 100-39-0 benzyl bromide 
• 98807-61-5 1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside 
• 19493-09-5 Methylenetriphenylphosphorane 
• 139070-99-8 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside 
• 127924-50-9 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(hydroxymethyl)-α-D-galactopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 138459-11-7 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside 
• 138459-06-0 Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 
• 138459-05-9 Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-6-O-(tert-butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 
• 139071-07-1 Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside 
• 139071-04-8 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranos-1-yl)-α-D-glucopyranoside 
• 138459-00-4 Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 139071-05-9 Methyl 4-C-(6-O-Acetyl-3,4,5,7-tetra-O-benzyl-2-heptulo-D-glucos-1-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside 
• 138459-02-6 (Z)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-02-6 (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-04-8 (Z)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-04-8 (E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-03-7 (Z)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose 
• 138459-03-7 (E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose 
• 127924-53-2 C₆₄H₆₆O₁₀ 

Relevant articles and documents

Preferred conformation of C-lactose at the free and peanut lectin bound states

A conformational analysis of methyl α-C-lactoside (5) is carried out (Table 1), which suggests the preferred solution conformation of 5 to be described as a mixture of conformers A (φ = 300°; ψ = 60°) and B (φ = 300°; ψ = 300°) to a first approximation. A

A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers

A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

A Highly Efficient and Chemoselective Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols

Various alcohols and phenols can be converted efficiently to the corresponding tetrahydropyranyl (THP) ethers in good yields using catalytic amounts of bromodimethylsulfonium bromide (0.005-0.02 equivalent) at room temperature. On the other hand, various THP ethers can also be deprotected to the parent alcoholic or phenolic compounds in CH2Cl2/ MeOH (5:2) by employing 0.05 equivalent of the same catalyst. Some of the major advantages of this procedure are its mild conditions, that it is highly selective and efficient, high yielding, and cost-effective, that it needs no solvent and is compatible with the presence of other protecting groups. Furthermore, no brominations occur at a double or triple bond, at an allylic position or even at an aromatic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.