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

Base Information

• Chemical Name: 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
• CAS No.: 872120-62-2
• Molecular Formula: C₄₈H₅₉NO₁₃Si
• Molecular Weight: 886.081
• Mol file: 872120-62-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 79.0%

(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) + benzoyl chloride (98-88-4) → 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:

With pyridine; In dichloromethane; at -40 ℃; for 1.5h;

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

Reference yield:

2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (152252-33-0) → 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 3 steps

1: 74 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 3 Angstroem / acetonitrile; CH₂Cl₂ / 0.08 h / -30 °C

2: 85 percent / sodium methoxide; Drierite / methanol / 44 h / 80 °C

3: 79 percent / pyridine / CH₂Cl₂ / 1.5 h / -40 °C

With pyridine; calcium sulfate; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; sodium methylate; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/anie.200501608

upstream 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

benzoyl chloride

(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

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