methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

Chemical Name:methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
CAS No.:920267-81-8
Molecular Formula:C₄₈H₄₈O₁₂
Molecular Weight:816.902
Hs Code.:

Synonyms:methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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Chemical Property of methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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Technology Process of methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 9 articles about methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-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: 70.0%

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

: 20672-67-7
methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

: methyl 2,3-anhydro-5,6-O-benzoyl-β-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

: 920267-81-8
methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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 3,4,6-tri-O-benzyl-α-D-mannopyranoside; 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

: 920267-81-8
methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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: 70 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

: 920267-81-8
methyl 2,3-anhydro-5,6-O-benzoyl-α-D-gulofuranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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: 70 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