1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol

Base Information

• Chemical Name: 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol
• CAS No.: 160835-85-8
• Molecular Formula: C₂₈H₃₀O₄
• Molecular Weight: 430.544
• Mol file: 160835-85-8.mol

Synonyms:1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol

Chemical Property of 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol

There total 2 articles about 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-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: 91.0%

2L-(2,4/3)-2,3,4-tri-O-benzyl-2-C-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one (160835-84-7) → 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol (160835-85-8)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol; dichloromethane; at -78 ℃;

DOI:10.1246/bcsj.67.1633

Reference yield:

(2S,3R,4S)-2,3,4-Tris-benzyloxy-5-hydroxy-2-methyl-cyclohexanone → 1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol (160835-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Ac₂O, pyridine / 12 h / Ambient temperature

2: 91 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; ethanol / -78 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; acetic anhydride; In ethanol; dichloromethane;

DOI:10.1246/bcsj.67.1633

Reference yield:

1D-(1,3/2,4)-2,3,4-tri-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol (160835-85-8) → 1D-3,4,5,6-tetra-O-benzyl-5-C-methyl-1,2,3,5/4,6-cyclohehanehexol

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF

2: OsO₄, 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 24 h / Irradiation

With osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In water; tert-butyl alcohol;

DOI:10.1246/bcsj.67.1633

upstream raw materials:

2L-(2,4/3)-2,3,4-tri-O-benzyl-2-C-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one

Downstream raw materials:

1D-(1,3/2,4)-1,2,3,4-tetra-O-benzyl-2-C-methyl-5-cyclohexene-1,2,3,4-tetrol