Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
• CAS No.: 205518-27-0
• Molecular Formula: C₆₃H₆₆O₁₃
• Molecular Weight: 1031.21
• Mol file: 205518-27-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-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: 63.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + Imidazole-1-carboxylic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (176787-45-4) → Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-27-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.3987/com-97-s84

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: 52 percent / NaH / tetrahydrofuran

With sodium hydride; triethylamine; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00272-9

Reference yield: 84.0%

Carbonic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-27-0) → methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-α-D-glucopyranoside (194208-51-0)

Guidance literature:

With silver perchlorate; tin(IV) chloride; In diethyl ether; at 20 ℃; for 2h;

DOI:10.3987/com-97-s84

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-galactopyranose

Imidazole-1-carboxylic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-α-D-glucopyranoside