(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

Base Information

• Chemical Name: (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
• CAS No.: 872120-61-1
• Molecular Formula: C₄₁H₅₅NO₁₂Si
• Molecular Weight: 781.973
• Mol file: 872120-61-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 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:

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

Multi-step reaction with 2 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

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

DOI:10.1002/anie.200501608

Reference yield:

(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 → (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:

Multi-step reaction with 2 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

With 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:

(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

Downstream raw materials:

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