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

Base Information

• Chemical Name: (-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate
• CAS No.: 147048-92-8
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 324.374
• Mol file: 147048-92-8.mol

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

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

There total 4 articles about (-)-methyl 5-O-benzyl-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: 73.0%

(+)-methyl 5-O-benzyl-4-deoxy-lyxo-D-hexonate (128503-22-0) + 2,2-dimethoxy-propane (77-76-9) → (-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate (147048-92-8)

Guidance literature:

With tin(ll) chloride; In 1,4-dioxane; at 20 ℃; for 24h;

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

Reference yield:

(+/-)-methyl 5-O-benzyl-4-deoxy-lyxo-DL-hexonate (128503-22-0,147048-87-1) + 2,2-dimethoxy-propane (77-76-9) → (+/-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-DL-lyxo-hexonate (147048-91-7,147048-92-8)

Guidance literature:

With tin(ll) chloride; In 1,4-dioxane; at 20 ℃; for 24h;

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

Reference yield:

(S)-((2S,4S)-4-Benzyloxy-5-hydroxy-tetrahydro-furan-2-yl)-hydroxy-acetic acid methyl ester → (-)-methyl 5-O-benzyl-4-deoxy-2,3-O-isopropylidene-D-lyxo-hexonate (147048-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 0 °C

2: SnCl₂ / dioxane / 24 h / 20 °C

With sodium tetrahydroborate; tin(ll) chloride; In 1,4-dioxane; methanol;

DOI:10.1016/S0040-4039(00)70712-X

upstream raw materials:

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

2,2-dimethoxy-propane

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

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

Downstream raw materials:

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

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

4-deoxy-D-mannopyranoside

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