methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate

Base Information

• Chemical Name: methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate
• CAS No.: 912942-90-6
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 912942-90-6.mol

Synonyms:methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate

Chemical Property of methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate

There total 2 articles about methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate 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: 88.0%

methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-ribo-heptofuranuronate (912942-93-9) → methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate (912942-90-6)

Guidance literature:

With [(R)-BINAP]RuBr₂; hydrogen; In methanol; at 45 ℃; for 24h; under 760 Torr;

DOI:10.1016/j.tetasy.2006.07.022

Reference yield:

1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid (120417-90-5) → methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate (912942-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 16 h / 20 °C

1.2: 58 percent / tetrahydrofuran / 20 °C

2.1: 88 percent / [((R)-Binap)RuBr₂]; hydrogen / methanol / 24 h / 45 °C / 760 Torr

With [(R)-BINAP]RuBr₂; hydrogen; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetasy.2006.07.022

Reference yield: 92.0%

methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-heptofuranuronate (912942-90-6) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose (912942-94-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2006.07.022

upstream raw materials:

methyl 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-ribo-heptofuranuronate

1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid

Downstream raw materials:

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-talo-hepto-1,4-furanose

5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-allo-hepto-1,4-furanose

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-triisopropylsilyl-β-L-talo-hepto-1,4-furanose

5-azido-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-7-O-triisopropylsilyl-α-D-allo-hepto-1,4-furanose