(R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester

Base Information

• Chemical Name: (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester
• CAS No.: 290301-28-9
• Molecular Formula: C₂₉H₄₀N₂O₁₂S
• Molecular Weight: 640.709
• Mol file: 290301-28-9.mol

Synonyms:(R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester

Chemical Property of (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester

There total 3 articles about (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl 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: 58.0%

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride (51224-18-1) + (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester (108957-20-6) → (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester (290301-28-9)

Guidance literature:

With sodium metabisulfite; potassium carbonate; In dimethyl sulfoxide; at 0 ℃; for 1.5h;

DOI:10.1016/S0960-894X(00)00223-7

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0) + N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) → (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester (290301-28-9)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0960-894X(00)00223-7

Reference yield:

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride (51224-18-1) → (R)-2-tert-Butoxycarbonylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanyl)-propionic acid benzyl ester (290301-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃; Na₂S₂O₅ / CH₂Cl₂; H₂O / 2 h / 20 °C

2: 1,1'-(azodicarbonyl)-dipiperidine; PBu₃ / tetrahydrofuran / 20 °C

With sodium metabisulfite; tributylphosphine; potassium carbonate; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; dichloromethane; water; 1: Hydrolysis / 2: Condensation;

DOI:10.1016/S0960-894X(00)00223-7

upstream raw materials:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose

N-tert-butoxycarbonyl-L-serine benzyl ester

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride

(R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester