(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

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Chemical Name:(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one
CAS No.:496065-38-4
Molecular Formula:C₂₇H₃₁N₃O₈
Molecular Weight:525.558
Hs Code.:

Synonyms:(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

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Chemical Property of (2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

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Technology Process of (2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

There total 4 articles about (2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one 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: 82.0%

: 496065-37-3
methyl 2-azido-3-O-(4-O-benzyl-3,6-dideoxy-β-D-ribo-hexopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 496065-38-4
(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

Guidance literature:: With acetic anhydride; dimethyl sulfoxide; at 20 ℃;
DOI:10.1139/v02-117

Reference yield:

: 96093-11-7
Methyl-2-azido-4,6-O-benzylidene-2-desoxy-β-D-galactopyranoside

: 496065-38-4
(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-iodosuccinimide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -60 °C

1.2: 83 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 3 h / -60 - -30 °C

2.1: 94 percent / sodium methoxide / methanol / 2 h

3.1: 82 percent / dimethyl sulfoxide; acetic anhydride / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; acetic anhydride; dimethyl sulfoxide; In methanol; dichloromethane; 2.1: Zemplen transesterification;
DOI:10.1139/v02-117

Reference yield:

: phenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-1-thio-α,β-D-ribo-hexopyranoside

: 496065-38-4
(2S,5S,6R)-2-((2S,4aR,6R,7R,8R,8aR)-7-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-benzyloxy-6-methyl-dihydro-pyran-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-iodosuccinimide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -60 °C

1.2: 83 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 3 h / -60 - -30 °C

2.1: 94 percent / sodium methoxide / methanol / 2 h

3.1: 82 percent / dimethyl sulfoxide; acetic anhydride / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; acetic anhydride; dimethyl sulfoxide; In methanol; dichloromethane; 2.1: Zemplen transesterification;
DOI:10.1139/v02-117