(S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester
• CAS No.: 1053654-18-4
• Molecular Formula: C₃₉H₄₁NO₁₀
• Molecular Weight: 683.755
• Mol file: 1053654-18-4.mol

Synonyms:

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

There total 3 articles about (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic 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:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (1053654-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

2: ZnCl₂ / tetrahydrofuran; diethyl ether / Ambient temperature

3: DMSO, acetic anhydride / 48 h / Ambient temperature

With 3,3-dimethyldioxirane; acetic anhydride; dimethyl sulfoxide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00086a047

Reference yield:

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (1053654-18-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂ / tetrahydrofuran; diethyl ether / Ambient temperature

2: DMSO, acetic anhydride / 48 h / Ambient temperature

With acetic anhydride; dimethyl sulfoxide; zinc(II) chloride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00086a047

Reference yield:

O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-N-Cbz-L-serine methyl ester (153947-45-6) → (S)-2-Benzyloxycarbonylamino-3-((2R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (1053654-18-4)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; for 48h; Ambient temperature;

DOI:10.1021/jo00086a047

upstream raw materials:

O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-N-Cbz-L-serine methyl ester

3,4,6-tri-O-benzyl-D-glucal

3,4,6-tri-O-benzyl-D-glucal epoxide

Downstream raw materials:

O-(3,4,6-Tri-O-benzyl-β-D-mannopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester