(2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone
• CAS No.: 134680-59-4
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 462.543

Synonyms:(2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

Chemical Property of (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

There total 9 articles about (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone 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: 75.0%

(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene (134680-57-2) → (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone (134680-59-4)

Guidance literature:

With hydrogen; acetic acid; Raney-Ni-W₄; In 1,4-dioxane; water; at 25 ℃; for 12h; under 760 Torr;

DOI:10.1016/0008-6215(91)89017-A

Reference yield: 70.0%

(3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol (134680-58-3) → (2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone (136892-47-2) + (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone (134680-59-4)

Guidance literature:

With hydrogen; acetic acid; Raney-Ni-W₄; In 1,4-dioxane; water; at 25 ℃; for 4h; under 760 Torr;

DOI:10.1016/0008-6215(91)89017-A

Reference yield: 65.0%

(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone (136892-47-2) → (2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone (134680-59-4)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 48h;

DOI:10.1016/0008-6215(91)89017-A

upstream raw materials:

(3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol

(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

Downstream raw materials:

1D-4,5,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-chiro-inositol

1D-4,5,6-tri-O-benzyl-2-deoxy-2-<<(1-methylethyl)diethylsilyl>oxy>methyl-chiro-inositol

Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexyl ester

(1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol

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