(2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 872120-60-0
• Molecular Formula: C₅₂H₆₆F₃NO₁₈Si
• Molecular Weight: 1078.17
• Mol file: 872120-60-0.mol

Synonyms:(2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 1 articles about (2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl 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: 74.0%

2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (152252-33-0) + (2S,4S,5R,6R)-4-Acetoxy-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester → (2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (872120-60-0) + (2S,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In dichloromethane; acetonitrile; at -30 ℃; for 0.0833333h;

DOI:10.1002/anie.200501608

Reference yield: 85.0%

(2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (872120-60-0) → (1R,3R,4R,8S)-8-Hydroxy-3-((1R,2R)-1,2,3-trihydroxy-propyl)-1-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-2-oxa-5-aza-bicyclo[2.2.2]octan-6-one (872120-61-1)

Guidance literature:

With calcium sulfate; sodium methylate; In methanol; at 80 ℃; for 44h;

DOI:10.1002/anie.200501608

Reference yield:

(2R,4S,5R,6R)-4-Acetoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (872120-60-0) → Benzoic acid (2R,3R)-2,3-dihydroxy-3-{(1R,3R,4R,8S)-8-hydroxy-6-oxo-1-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-2-oxa-5-aza-bicyclo[2.2.2]oct-3-yl}-propyl ester (872120-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / sodium methoxide; Drierite / methanol / 44 h / 80 °C

2: 79 percent / pyridine / CH₂Cl₂ / 1.5 h / -40 °C

With pyridine; calcium sulfate; sodium methylate; In methanol; dichloromethane;

DOI:10.1002/anie.200501608

upstream raw materials:

2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

(1R,3R,4R,8S)-8-Hydroxy-3-((1R,2R)-1,2,3-trihydroxy-propyl)-1-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-2-oxa-5-aza-bicyclo[2.2.2]octan-6-one

Benzoic acid (2R,3R)-2,3-dihydroxy-3-{(1R,3R,4R,8S)-8-hydroxy-6-oxo-1-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-2-oxa-5-aza-bicyclo[2.2.2]oct-3-yl}-propyl ester