methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 257936-68-8
• Molecular Formula: C₇₂H₈₅F₃O₁₉S
• Molecular Weight: 1343.52

Synonyms:methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 9 articles about methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-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: 87.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl O-(6-deoxy-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (257936-78-0) → methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (257936-68-8)

Guidance literature:

With pyridine; In dichloromethane; at -60 - 10 ℃;

DOI:10.1071/CH99031

Reference yield:

phenyl 1-thio-β-D-fucopyranoside (1214-98-8) → methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (257936-68-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: TsOH*H₂O / 4 h / 20 °C

2.1: 89 percent / 4-dimethylaminopyridine; pyridine / 20 - 100 °C

3.1: aq. TFA / 20 °C

4.1: Bu₂SnO / benzene / Heating

4.2: 1,2-dichloro-ethane / 1 h / 20 °C

5.1: 89 percent / pyridine / CH₂Cl₂ / 20 °C

6.1: 82 percent / N-iodosuccinimide; TfOH / 1,2-dichloro-ethane; diethyl ether / 20 °C

7.1: 91 percent / thiourea; 2,6-lutidine / CH₂Cl₂; methanol / Heating

8.1: 87 percent / pyridine / CH₂Cl₂ / -60 - 10 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; di(n-butyl)tin oxide; toluene-4-sulfonic acid; thiourea; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene; 1.1: cyclocondensation / 2.1: Esterification / 3.1: Ring cleavage / 4.1: Cyclization / 4.2: Ring cleavage / 5.1: Acetylation / 6.1: Substitution / 7.1: Deacetylation / 8.1: Esterification;

DOI:10.1071/CH99031

Reference yield:

Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid (141193-62-6) → methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (257936-68-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaOMe / methanol

2.1: TsOH*H₂O / 4 h / 20 °C

3.1: 89 percent / 4-dimethylaminopyridine; pyridine / 20 - 100 °C

4.1: aq. TFA / 20 °C

5.1: Bu₂SnO / benzene / Heating

5.2: 1,2-dichloro-ethane / 1 h / 20 °C

6.1: 89 percent / pyridine / CH₂Cl₂ / 20 °C

7.1: 82 percent / N-iodosuccinimide; TfOH / 1,2-dichloro-ethane; diethyl ether / 20 °C

8.1: 91 percent / thiourea; 2,6-lutidine / CH₂Cl₂; methanol / Heating

9.1: 87 percent / pyridine / CH₂Cl₂ / -60 - 10 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; thiourea; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene; 1.1: Deacetylation / 2.1: cyclocondensation / 3.1: Esterification / 4.1: Ring cleavage / 5.1: Cyclization / 5.2: Ring cleavage / 6.1: Acetylation / 7.1: Substitution / 8.1: Deacetylation / 9.1: Esterification;

DOI:10.1071/CH99031

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl O-(6-deoxy-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

phenyl 1-thio-β-D-fucopyranoside

Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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