methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside
• CAS No.: 824410-29-9
• Molecular Formula: C₄₈H₅₄O₁₃
• Molecular Weight: 838.949
• Mol file: 824410-29-9.mol

Synonyms:

Chemical Property of methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside

There total 1 articles about methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside (824410-14-2) → methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside (824410-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / indium; phosphate buffer / tetrahydrofuran / 2 h / pH 7

2: 51 mg / pyridine / 16 h / 20 °C

With pyridine; indium; phosphate buffer; In tetrahydrofuran; 1: Barbier-type allylation;

DOI:10.1016/j.carres.2004.09.010

Reference yield:

methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside (824410-29-9) → 1-((2S,3R,4S,5R,2'S,3'R,4'S,5'R,6'R)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-4,5,6-trihydroxy-octahydro-[2,2']bipyranyl-3-yl)-ethanone

Guidance literature:

methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside; With lithium hydroxide; In methanol; water; at 20 ℃; for 0.5h;

With hydrogenchloride; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2004.09.010

Reference yield:

methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside (824410-29-9) → Acetic acid (S)-((2R,3S,4S,5R,6S)-4,5-diacetoxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl ester

Guidance literature:

methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

With phosphate buffer; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 1h; pH=7;

DOI:10.1016/j.carres.2004.09.010

upstream raw materials:

methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside