methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
CAS No.:920267-96-5
Molecular Formula:C₆₄H₆₈O₁₇
Molecular Weight:1109.23
Hs Code.:

methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Synonyms:methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

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Chemical Property of methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

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Technology Process of methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

There total 10 articles about methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 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: 59.0%

: 920274-28-8
2,3-anhydro-5,6-di-O-benzoyl-β-D-gulofuranosyl-p-tolyl-(R/S)-sulfoxide

: methyl 3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

: 920267-96-5
methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: 2,3-anhydro-5,6-di-O-benzoyl-β-D-gulofuranosyl-p-tolyl-(R/S)-sulfoxide; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; In dichloromethane; at -78 - -40 ℃;

methyl 3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside; In dichloromethane; at -40 ℃;
DOI:10.1021/jo061713o

Reference yield:

: (1R,2S,4S,5R)-2-((R)-2-Methoxy-2-methyl-[1,3]dioxolan-4-yl)-4-p-tolylsulfanyl-3,6-dioxa-bicyclo[3.1.0]hexane

: 920267-96-5
methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. HCl / ethyl acetate / 20 °C

1.2: 1.32 g / NaOCH₃ / methanol; CH₂Cl₂ / 14 h / 20 °C / pH 10

2.1: 90 percent / pyridine / 12 h / 20 °C

3.1: 54 percent / m-CPBA / CH₂Cl₂ / -78 - 20 °C

4.1: 2,6-di-tert-butyl-4-methylpyridine; Tf₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / -78 - -40 °C

4.2: 59 percent / CH₂Cl₂ / -40 °C

With pyridine; hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;
DOI:10.1021/jo061713o

Reference yield:

: 920267-59-0
p-tolyl 2,3-anhydro-1-thio-β-D-gulofuranoside

: 920267-96-5
methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-α-D-galactofuranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / pyridine / 12 h / 20 °C

2.1: 54 percent / m-CPBA / CH₂Cl₂ / -78 - 20 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine; Tf₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / -78 - -40 °C

3.2: 59 percent / CH₂Cl₂ / -40 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/jo061713o