pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Base Information

• Chemical Name: pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside
• CAS No.: 150772-65-9
• Molecular Formula: C₅₁H₆₀ClNO₁₃
• Molecular Weight: 930.489
• Mol file: 150772-65-9.mol

Synonyms:pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Chemical Property of pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside

There total 4 articles about pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside 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:

pent-4-enyl 2,6-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside (150772-56-8) → pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (150772-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / TMSOTf, molecular sieves 4A / toluene / 2 h / -20 °C

2: 1.) MeNH₂, 3.) Et₃N

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine; methylamine; In toluene;

DOI:10.1021/ja00070a048

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate (150772-55-7) → pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (150772-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / TMSOTf, molecular sieves 4A / toluene / 2 h / -20 °C

2: 1.) MeNH₂, 3.) Et₃N

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine; methylamine; In toluene;

DOI:10.1021/ja00070a048

Reference yield:

acetic anhydride (108-24-7) + Chloro-acetic acid (2R,3R,4R,5S,6S)-3-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethyl ester → pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside (150772-65-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 2h;

DOI:10.1021/ja00110a011

upstream raw materials:

acetic anhydride

pent-4-enyl 2,6-di-O-acetyl-3-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-α-D-mannopyranoside

Chloroacetic anhydride

pent-4-enyl 2,6-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1-4)-O-(2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranosyl)-(1-4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inosito