Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 93636-33-0
• Molecular Formula: C₂₈H₃₀O₇
• Molecular Weight: 478.542
• Mol file: 93636-33-0.mol

Synonyms:Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester

There total 3 articles about Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester 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: 59.0%

methyl 4,6-di-O-benzyl-α-D-mannopyranoside (73045-57-5) + benzoyl chloride (98-88-4) → Benzoic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93636-34-1) + Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester (93636-33-0) + C35H34O8 (93636-35-2)

Guidance literature:

With sodium hydroxide; sodium acetate; trimethylbenzylammonium bromide; In benzene; Ambient temperature;

DOI:10.1016/0008-6215(87)80212-4

Reference yield: 50.0%

methyl 4,6-di-O-benzyl-α-D-mannopyranoside (73045-57-5) + benzoic acid anhydride (93-97-0) → Benzoic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93636-34-1) + Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester (93636-33-0) + C35H34O8 (93636-35-2)

Guidance literature:

With sodium hydroxide; sodium acetate; benzyltriethylammonium bromide; In benzene; Ambient temperature;

DOI:10.1016/0008-6215(87)80212-4

Reference yield: 36.0%

methyl 4,6-di-O-benzyl-α-D-mannopyranoside (73045-57-5) + benzoyl chloride (98-88-4) → Benzoic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93636-34-1) + Benzoic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester (93636-33-0)

Guidance literature:

With sodium hydride; copper dichloride; In various solvent(s); 1.) 1 h, reflux, 2.) overnight, room temperature;

DOI:10.1016/S0008-6215(00)90642-6

upstream raw materials:

methyl 4,6-di-O-benzyl-α-D-mannopyranoside

benzoyl chloride

benzoic acid anhydride

Downstream raw materials:

methyl 4,6-di-O-benzyl-2-O-(3'',4'',6''-tri-O-benzyl-α-D-galactopyranosyl)-3-O-(4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-2',2''-di-O-methylene-α-D-mannopyranoside

methyl 4,6-di-O-benzyl-2-O-(3'',4'',6''-tri-O-benzyl-α-D-galactopyranosyl)-3-O-(4'-O-benzyl-3',6'-dideoxy-α-D-xylohexopyranosyl)-α-D-mannopyranoside

methyl 4,6-di-O-benzyl-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

methyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylohexopyranosyl)-α-D-mannopyranoside