Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester
• CAS No.: 317816-84-5
• Molecular Formula: C₂₃H₃₁NO₉Se
• Molecular Weight: 544.46
• Mol file: 317816-84-5.mol

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl 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: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside (150809-76-0) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester (317816-84-5)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside; With 1.3-propanedithiol; triethylamine;

di-tert-butyl dicarbonate; Further stages.;

DOI:10.1021/ol006682c

Reference yield:

diphenyl diselenide (1666-13-3) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester (317816-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaN₃; PhI(OAc)2

2: 80 percent / Et₃N; HS(CH₂)3SH

With 1.3-propanedithiol; sodium azide; [bis(acetoxy)iodo]benzene; triethylamine; 1: Addition / 2: Reduction / 2: Acylation;

DOI:10.1021/ol006682c

Reference yield:

triacetyl-D-galactal (4098-06-0) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-phenylselanyl-tetrahydro-pyran-4-yl ester (317816-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaN₃; PhI(OAc)2

2: 80 percent / Et₃N; HS(CH₂)3SH

With 1.3-propanedithiol; sodium azide; [bis(acetoxy)iodo]benzene; triethylamine; 1: Addition / 2: Reduction / 2: Acylation;

DOI:10.1021/ol006682c

upstream raw materials:

di-tert-butyl dicarbonate

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside

diphenyl diselenide

triacetyl-D-galactal