(1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol

Base Information

• Chemical Name: (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol
• CAS No.: 73111-27-0
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532

Synonyms:(1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol

Chemical Property of (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol

Chemical Property:

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Technology Process of (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol

There total 9 articles about (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol 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: 100.0%

N-((1R,2S,3R)-1,2,3-Tris-benzyloxy-pent-4-enyl)-formimidic acid → (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol (73111-27-0)

Guidance literature:

In toluene; at 110 ℃;

DOI:10.1055/s-1998-1969

Reference yield: 100.0%

2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime (219586-93-3) → (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol (73111-27-0)

Guidance literature:

In toluene; for 15h; Heating;

DOI:10.1039/a905706d

Reference yield: 96.0%

(3aR,4R,5S,6S)-4,5,6-tris(benzyloxy)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole (260415-86-9) → (1R,5R,6R,7S,8S)-6,7,8-tri-O-benzyl-3-oxa-2-azabicyclo[3.3.0]octane-6,7,8-triol (73111-27-0)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(99)00991-6

upstream raw materials:

methyl tri-O-benzyl-6-bromo-β-D-6-deoxy-glucopyranoside

2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime

(3aR,4R,5S,6S)-4,5,6-tris(benzyloxy)-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole

2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose

Downstream raw materials:

((1R)-2c-amino-3t,4c,5t-tris-benzyloxy-cyclopentyl)-methanol

(3aR)-4c,5t,6c-tris-benzyloxy-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole-1-carboxylic acid phenyl ester

((1R)-2t,3c,4t-tris-benzyloxy-5c-hydroxymethyl-cyclopentyl)-carbamic acid phenyl ester

(4aR)-5c,6t,7c-tris-benzyloxy-(4ar,7ac)-hexahydro-cyclopenta[d][1,3]oxazine-1-carboxylic acid phenyl ester

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