methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside

Base Information

• Chemical Name: methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside
• CAS No.: 130050-87-2
• Molecular Formula: C₆₂H₇₀ClNO₁₉
• Molecular Weight: 1168.69
• Mol file: 130050-87-2.mol

Synonyms:methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside

Chemical Property of methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside

There total 4 articles about methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside 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: 66.0%

ethyl 3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-1-thio-β-D-glucopyranose (118545-27-0) + methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside (118266-82-3,119645-05-5,130144-09-1) → methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside (130050-87-2)

Guidance literature:

With methylsulfenyl bromide; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/0008-6215(90)84082-6

Reference yield:

phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (87470-73-3,120403-26-1,38184-12-2) → methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside (130050-87-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.2 g / pyridine

2: 83 percent / methylsulfenyl bromide, molecular sieve (4 Angstroem) / CH₂Cl₂ / 15 h / 22 °C

3: 0.54 g / NaOCH₃ / methanol; CH₂Cl₂

4: 66 percent / methylsulfenyl bromide, silver triflate / CH₂Cl₂

With pyridine; methylsulfenyl bromide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(90)84082-6

Reference yield:

phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (120403-27-2,38184-11-1) → methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-glucopyranoside (130050-87-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / methylsulfenyl bromide, molecular sieve (4 Angstroem) / CH₂Cl₂ / 15 h / 22 °C

2: 0.54 g / NaOCH₃ / methanol; CH₂Cl₂

3: 66 percent / methylsulfenyl bromide, silver triflate / CH₂Cl₂

With methylsulfenyl bromide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(90)84082-6

upstream raw materials:

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

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside