Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 204579-09-9
• Molecular Formula: C₄₇H₅₃NO₈Si
• Molecular Weight: 788.025

Synonyms:Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

There total 2 articles about Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl 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:

2-(trimethylsilyl)-ethoxycarbonyl chloride (20160-60-5) → Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-09-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 1) LHMDS / 1) THF, -78 deg C, 2) THF, 0 deg C

With lithium hexamethyldisilazane;

DOI:10.1021/jo980024c

Reference yield:

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose (204579-03-3) → Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-09-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 1) LHMDS / 1) THF, -78 deg C, 2) THF, 0 deg C

With lithium hexamethyldisilazane;

DOI:10.1021/jo980024c

Reference yield: 3.0%

Benzoyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-09-9) → N-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzamide + N-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzamide

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/jo980024c

upstream raw materials:

2-(trimethylsilyl)-ethoxycarbonyl chloride

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose

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