2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone

Base Information

• Chemical Name: 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone
• CAS No.: 306968-48-9
• Molecular Formula: C₃₅H₃₆O₆
• Molecular Weight: 552.667
• Mol file: 306968-48-9.mol

Synonyms:2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone

Chemical Property of 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone

There total 4 articles about 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone 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: 49.0%

(2S,3S,4S,5S)-2,3,4-tri-O-benzyl-5-C-<(benzyloxy)methyl>-6,6-dichloro-1-oxo-2,3,4,5-cyclohexanetetrol → 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone (306968-48-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Reflux; Inert atmosphere;

DOI:10.1021/ja3041866

Reference yield:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol (306968-47-8) → 2L-(2,3,5/4)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone + 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone (306968-48-9)

Guidance literature:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol; With acetic anhydride; dimethyl sulfoxide; at 20 ℃;

With zinc(II) chloride; In tetrahydrofuran; water; Heating;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol (306968-50-3) → 2L-(2,3,5/4)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone + 2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone (306968-48-9)

Guidance literature:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol; With acetic anhydride; dimethyl sulfoxide; at 20 ℃;

With zinc(II) chloride; In tetrahydrofuran; water; Heating;

DOI:10.1016/S0040-4020(00)00621-9

upstream raw materials:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol

Downstream raw materials:

1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

2-epi-valiolone