(-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate

Base Information

• Chemical Name: (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate
• CAS No.: 128503-23-1
• Molecular Formula: C₂₃H₃₈O₆Si
• Molecular Weight: 438.637
• Mol file: 128503-23-1.mol

Synonyms:(-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate

Chemical Property of (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate

There total 6 articles about (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate 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: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate (147048-92-8) → (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate (128503-23-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/S0040-4020(01)88356-3

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (+/-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-DL-lyxo-hexonate (147048-91-7,147048-92-8) → (+/-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-DL-lyxo-hexonate (128503-23-1,147048-93-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/S0040-4020(01)88356-3

Reference yield:

(+)-methyl 5-O-benzyl-4-deoxy-lyxo-D-hexonate (128503-22-0) → (-)-methyl 5-O-benzyl-6-O-t-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate (128503-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / SnCl₂ / dioxane / 24 h / 20 °C

2: 98 percent / imidazole / dimethylformamide / 0 °C

With 1H-imidazole; tin(ll) chloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88356-3

upstream raw materials:

tert-butyldimethylsilyl chloride

(-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate

(+)-methyl 5-O-benzyl-4-deoxy-lyxo-D-hexonate

(-)-5-O-acetyl-2-O-benzyl-3-deoxy-β-D-arabino-hexofuranurono-6,1-lactone

Downstream raw materials:

(-)-5-O-benzyl-6-O-(t-butyl)dimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexose

4-deoxy-D-mannopyranoside

(+/-)-5-O-benzyl-6-O-(t-butyl)dimethylsilyl-4-deoxy-2,3-O-isopropylidene-DL-lyxo-hexose

(+/-)-methyl 4-deoxy-DL-lyxo-hexopyranoside