methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
CAS No.:115678-24-5
Molecular Formula:C₃₅H₄₄O₁₃S
Molecular Weight:704.793
Hs Code.:

Synonyms:methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

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Technology Process of methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 7 articles about methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 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: 42.0%

: 61303-35-3
2,3,4,6-tetra-O-acetyl-α-L mannopyranosyl bromide

: 115678-13-2
methyl 3,4-di-O-benzyl-6-deoxy-1-thio-α-L-mannopyranoside

: 115678-24-5
methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at -40 - 25 ℃; for 2.5h;
DOI:10.1021/jo00252a030

Reference yield:

: 100-39-0
benzyl bromide

: 115678-24-5
methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 1 h, 2.) 10 deg C, 2 h

2: 86.4 percent / trifluoroacetic acid / methanol / 2 h / 50 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylamonium bromide / 1.) C₆H₆, reflux, 5 h, 2.) 50 deg C, 3 h

4: 42 percent / 4-A molecular sieves, N,N,N'N'-tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -40 - 25 °C

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; tetramethylurea; In methanol; dichloromethane;
DOI:10.1021/jo00252a030

Reference yield:

: 115678-10-9
methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 115678-24-5
methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 1 h, 2.) 10 deg C, 2 h

2: 86.4 percent / trifluoroacetic acid / methanol / 2 h / 50 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylamonium bromide / 1.) C₆H₆, reflux, 5 h, 2.) 50 deg C, 3 h

4: 42 percent / 4-A molecular sieves, N,N,N'N'-tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h / -40 - 25 °C

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; tetramethylurea; In methanol; dichloromethane;
DOI:10.1021/jo00252a030