1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol

Base Information

• Chemical Name: 1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol
• CAS No.: 157761-62-1
• Molecular Formula: C₂₈H₂₉N₃O₄
• Molecular Weight: 471.556

Synonyms:1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol

Chemical Property of 1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol

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Technology Process of 1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol

There total 1 articles about 1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol 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: 41.0%

(1R,2R,3S,4R,6R)-2,3,4-Tris-benzyloxy-5-methylene-7-oxa-bicyclo[4.1.0]heptane (157761-57-4) → 1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol (157761-62-1) + 1S(1,3/2,4)-6-azidomethyl-1,2,3-tri-O-benzyl-5-enecyclohexane-1,2,3,4-tetrol (157761-61-0) + 1S(1,2,4/3,6)-1-azido-2,3,4-tri-O-benzyl-5-methylenecyclohexane-2,3,4,6-tetrol

Guidance literature:

With sodium azide; ammonium chloride;

DOI:10.1016/S0040-4039(00)60726-8

Reference yield: 88.0%

1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol (157761-62-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol (157761-68-7)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at -30 ℃;

DOI:10.1016/S0040-4039(00)60726-8

Reference yield:

1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol (157761-62-1) → (1R,2S,4R,5S,6S)-2-Amino-4,5,6-tris-benzyloxy-3-methylene-cyclohexanol

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/S0040-4039(00)60726-8

upstream raw materials:

(1R,2R,3S,4R,6R)-2,3,4-Tris-benzyloxy-5-methylene-7-oxa-bicyclo[4.1.0]heptane

Downstream raw materials:

2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1R(1,3,5/2,4)-1-azido-3,4,5-tri-O-benzyl-6-methylenecyclohexane-2,3,4,5-tetrol

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