Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

Base Information

Chemical Name:Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide
CAS No.:151988-24-8
Molecular Formula:C₆₁H₇₄O₁₄S
Molecular Weight:1063.32
Hs Code.:

Synonyms:Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

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Chemical Property of Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

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Technology Process of Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

There total 11 articles about Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide 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: 98.0%

: 151988-23-7
Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

: 151988-24-8
Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃;

Reference yield:

: 151988-22-6
Phenyl 2,3,4-Tri-O-pivaloyl-1-thio-β-D-glucopyranoside

: 151988-24-8
Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

Guidance literature:: Multi-step reaction with 2 steps

1: 68 percent / 2,6-di-tert-butyl-pyridine; triflic anhydride / CH₂Cl₂; diethyl ether / 0.5 h / -78 - 0 °C

2: 93 percent / mCPBA / CH₂Cl₂ / -78 - 10 °C

With 2,6-di-tert-butyl-pyridine; trifluoromethylsulfonic anhydride; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; 1: Condensation / 2: Oxidation;

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 151988-24-8
Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 16 h / 50 °C

2: 2.3 g / pyridine / 168000 h / 20 °C

3: 84.8 percent / TFA / CH₂Cl₂ / 0.17 h / 0 °C

4: 68 percent / 2,6-di-tert-butyl-pyridine; triflic anhydride / CH₂Cl₂; diethyl ether / 0.5 h / -78 - 0 °C

5: 93 percent / mCPBA / CH₂Cl₂ / -78 - 10 °C

With pyridine; 2,6-di-tert-butyl-pyridine; trifluoromethylsulfonic anhydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In diethyl ether; dichloromethane; 1: Etherification / 2: Acylation / 3: detritylation / 4: Condensation / 5: Oxidation;