methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside
CAS No.:151967-75-8
Molecular Formula:C₃₃H₃₇N₃O₁₃S
Molecular Weight:715.735
Hs Code.:

Synonyms:methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

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Technology Process of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

There total 8 articles about methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-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%

: 145836-01-7
Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

: 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl chloride

: 151967-75-8
methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With 2,4,6-trimethyl-pyridine; silver perchlorate; In dichloromethane; 1.) 0 deg C, 30 min, 2.) 30 min;
DOI:10.1016/0008-6215(93)80073-N

Reference yield:

: 115678-08-5
methyl 1-thio-α-L-rhamnopyranoside

: 151967-75-8
methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) dibutyltin oxide, molecular sieves (4 Angstroem), 2.) CsF / 1.) toluene, relux, 2 h, 2.) DMF, r.t., 18 h

2: 90 percent / pyridine / 18 h / 50 °C

3: 65 percent / H₂ / 5percent Pd/C / 1.) 2-methoxyethanol, r.t., overnight, 2.) DMF, r.t., 18 h, 3.) DMF, 2-methoxyethanol, 18 h

4: 10 mg / 2,4,6-trimethylpyridine, silver triflate / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) r.t., 30 min

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; cesium fluoride; palladium on activated charcoal; In dichloromethane;
DOI:10.1016/0008-6215(93)80073-N

Reference yield:

: 145836-01-7
Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

: 151967-76-9
O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride

: 151967-75-8
methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

: 151967-77-0
methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; 1.) 0 deg C, 10 min, 2.) r.t., 30 min;
DOI:10.1016/0008-6215(93)80073-N