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

Base Information

• Chemical Name: Carbonic acid cyclohexylmethyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
• CAS No.: 205518-20-3
• Molecular Formula: C₄₂H₄₈O₈
• Molecular Weight: 680.838

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

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

Chemical Property:

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

There total 2 articles about Carbonic acid cyclohexylmethyl ester (3R,4S,5R,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: 97.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + carbonic acid cyclohexylmethyl ester 4-nitro-phenyl ester (176787-43-2) → Carbonic acid cyclohexylmethyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-20-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00272-9 DOI:10.3987/com-97-s84

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Carbonic acid cyclohexylmethyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: 97 percent / NaH / tetrahydrofuran

With sodium hydride; triethylamine; In tetrahydrofuran;

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

Reference yield: 80.0%

Carbonic acid cyclohexylmethyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (205518-20-3) → cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74709-50-5) + cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (74741-49-4)

Guidance literature:

With Cp₂HfCl₂-2AgClO₄; In diethyl ether; at 20 ℃; for 5h; Yields of byproduct given;

DOI:10.3987/com-97-s84

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

carbonic acid cyclohexylmethyl ester 4-nitro-phenyl ester

benzyl alcohol

Downstream raw materials:

cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

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

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