benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside

Base Information

• Chemical Name: benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside
• CAS No.: 161955-20-0
• Molecular Formula: C₂₃H₃₄O₈
• Molecular Weight: 438.518
• Mol file: 161955-20-0.mol

Synonyms:benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside

Chemical Property of benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside

There total 7 articles about benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside 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: 76.0%

benzyl 3,6-di-O-pivaloyl-2,4-bis(O-trifluoromethylsulfonyl)-β-D-galactopyranoside (161955-14-2) → benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside (161955-20-0)

Guidance literature:

benzyl 3,6-di-O-pivaloyl-2,4-bis(O-trifluoromethylsulfonyl)-β-D-galactopyranoside; With 18-crown-6 ether; cesium trifluoroacetate; In N,N-dimethyl-formamide; toluene; at 80 ℃;

With pyridine; sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 1h;

DOI:10.1246/bcsj.70.885

Reference yield:

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-13-2,30657-70-6,31281-76-2,53729-76-3,142696-63-7,83113-54-6) → benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside (161955-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / NaOMe; methanol / pH 9

2.1: bis(tributyltin) oxide / toluene / 3 h / Heating

2.2: 86 percent / toluene / 24 h / 0 - 20 °C

3.1: 98 percent / pyridine / CH₂Cl₂ / -19 - 20 °C

4.1: 18-crown-6; cesium trifluoroacetate / toluene; dimethylformamide / 80 °C

4.2: 76 percent / pyridine; sodium hydrogencarbonate / methanol; H₂O / 1 h / 20 °C

With pyridine; methanol; 18-crown-6 ether; sodium methylate; cesium trifluoroacetate; bis(tri-n-butyltin)oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Deacetylation / 2.1: Condensation / 2.2: Acylation / 3.1: sulfonylation / 4.1: Substitution / 4.2: Hydrolysis;

DOI:10.1246/bcsj.70.885

Reference yield:

benzyl 3,6-di-O-pivaloyl-β-D-galactopyranoside (161955-13-1) → benzyl 3,6-di-O-pivaloyl-β-D-mannopyranoside (161955-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / pyridine / CH₂Cl₂ / -19 - 20 °C

2.1: 18-crown-6; cesium trifluoroacetate / toluene; dimethylformamide / 80 °C

2.2: 76 percent / pyridine; sodium hydrogencarbonate / methanol; H₂O / 1 h / 20 °C

With pyridine; 18-crown-6 ether; cesium trifluoroacetate; In dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: sulfonylation / 2.1: Substitution / 2.2: Hydrolysis;

DOI:10.1246/bcsj.70.885

upstream raw materials:

cesium trifluoroacetate

benzyl 3,6-di-O-pivaloyl-2,4-bis(O-trifluoromethylsulfonyl)-β-D-galactopyranoside

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

benzyl 3,6-di-O-pivaloyl-β-D-galactopyranoside

Downstream raw materials:

benzyl 2,4-bis(O-methoxymethyl)-3,6-di-O-pivaloyl-β-D-mannopyranoside

Refernces

• 1、 Sato, Ken-ichi,Yoshitomo, Akira. "A Novel Method for Constructions of β-D-Mannosidic, 2-Acetamido-2-deoxy-β-D-mannosidic, and 2-Deoxy-β-D-arabino-hexopyranosidic Units from the Bis(triflate) Derivative of β-D-Galactoside". . p. 39 - 40. Retrieved 2007/10/02.