methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

Base Information

Chemical Name:methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside
CAS No.:801287-89-8
Molecular Formula:C₂₈H₃₄O₁₅
Molecular Weight:610.569
Hs Code.:

Synonyms:methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

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Technology Process of methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

There total 4 articles about methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside 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: 78.0%

: 801287-88-7
methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α,β-D-xylo-hex-5-enopyranosyde

: 801287-89-8
methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 20 ℃; for 9h;
DOI:10.1016/j.carres.2004.07.022

Reference yield:

: (2R,4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 801287-89-8
methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: Ph₃P; imidazole; I₂ / toluene / 3 h / 90 °C

2: 92 percent / 4-dimethylaminopyridine / pyridine / 15 h

3: 80 percent / AgF / pyridine / 21 h / 20 °C

4: 78 percent / 3-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂; H₂O / 9 h / 20 °C

With 1H-imidazole; dmap; iodine; silver fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In pyridine; dichloromethane; water; toluene;
DOI:10.1016/j.carres.2004.07.022

Reference yield:

: 808737-09-9
(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 801287-89-8
methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / 4-dimethylaminopyridine / pyridine / 15 h

2: 80 percent / AgF / pyridine / 21 h / 20 °C

3: 78 percent / 3-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂; H₂O / 9 h / 20 °C

With dmap; silver fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; water;
DOI:10.1016/j.carres.2004.07.022