((2R,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: ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 204579-04-4
• Molecular Formula: C₄₀H₄₉NO₇Si
• Molecular Weight: 683.917
• Mol file: 204579-04-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ((2R,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) + 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose (204579-03-3) → ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-04-4) + ((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-05-5)

Guidance literature:

Yield given. Yields of byproduct given;

DOI:10.1021/jo980024c

Reference yield:

((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-04-4) → Cyclohexanecarboxylic acid ((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-amide

Guidance literature:

Multi-step reaction with 2 steps

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

2: 92 percent / TBAF / tetrahydrofuran / 0 °C

With dmap; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo980024c

Reference yield:

((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (204579-04-4) → 1-acetamido-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

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

2: 96 percent / TBAF / tetrahydrofuran / 0 °C

With tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo980024c

upstream raw materials:

2-(trimethylsilyl)-ethoxycarbonyl chloride

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

Downstream raw materials:

Oxo-[(2-trimethylsilanyl-ethoxycarbonyl)-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-amino]-acetic acid methyl ester

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

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

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