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

Base Information

Chemical Name: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
CAS No.:151967-76-9
Molecular Formula:C₃₂H₃₄ClN₃O₁₃
Molecular Weight:704.087
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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: 85.0%

: 142967-73-5
methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-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

Guidance literature:: With Dichloromethyl methyl ether; zinc(II) chloride; In chloroform; at 50 - 55 ℃; for 7h;
DOI:10.1016/0008-6215(93)80073-N

Reference yield:

: 115678-08-5
methyl 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

Guidance literature:: Multi-step reaction with 5 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

5: Cl₂ / CCl₄; CDCl₃

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; chlorine; di(n-butyl)tin oxide; cesium fluoride; palladium on activated charcoal; In tetrachloromethane; chloroform-d1; dichloromethane;
DOI:10.1016/0008-6215(93)80073-N

Reference yield:

: 120255-47-2
(2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / pyridine / 18 h / 50 °C

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

3: 10 mg / 2,4,6-trimethylpyridine, silver triflate / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) r.t., 30 min

4: Cl₂ / CCl₄; CDCl₃

With pyridine; 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; chlorine; palladium on activated charcoal; In tetrachloromethane; chloroform-d1; dichloromethane;
DOI:10.1016/0008-6215(93)80073-N