(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 870001-67-5
• Molecular Formula: C₄₄H₅₅N₃O₁₅Si
• Molecular Weight: 894.017

Synonyms:(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Chemical Property of (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

There total 14 articles about (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 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:

4-Oxo-pentanoic acid (2R,3R,4R,5S,6R)-2-((1S,3S,4R,5S,8S)-4-acetoxy-3-methoxy-7-oxo-2,6-dioxa-bicyclo[3.2.1]oct-8-yloxy)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid (870001-67-5)

Guidance literature:

With silica gel; In hexane; dichloromethane; at 20 ℃;

DOI:10.1021/ol052130o

Reference yield:

methyl 2-O-acetyl-α-D-3,6-glucuronolactone (870001-63-1) → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid (870001-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

1.2: CH₂Cl₂ / 20 h / -60 - 20 °C

2.1: 0.074 g / silica gel / CH₂Cl₂; hexane / 20 °C

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; silica gel; 2,6-di-tert-butyl-4-methylpyridine; In hexane; dichloromethane;

DOI:10.1021/ol052130o

Reference yield:

(1S,3S,4R,5R,8S)-4-Hydroxy-3-methoxy-8-(4-methoxy-benzyloxy)-2,6-dioxa-bicyclo[3.2.1]octan-7-one → (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid (870001-67-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.457 g / 4 h / 75 °C

2.1: 65 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 12 h / 0 °C

3.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

3.2: CH₂Cl₂ / 20 h / -60 - 20 °C

4.1: 0.074 g / silica gel / CH₂Cl₂; hexane / 20 °C

With ammonium cerium(IV) nitrate; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; silica gel; 2,6-di-tert-butyl-4-methylpyridine; In hexane; dichloromethane; water; acetonitrile;

DOI:10.1021/ol052130o

upstream raw materials:

methyl 2-O-acetyl-α-D-3,6-glucuronolactone

methyl 2-O-acetyl-4-(p-methoxybenzyl)-α-D-3,6-glucuronolactone

(2S,3S,4S,5R,6S)-4,5-Diacetoxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester

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