ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Base Information

• Chemical Name: ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate
• CAS No.: 115828-14-3
• Molecular Formula: C₂₅H₄₀O₆Si
• Molecular Weight: 464.674
• Mol file: 115828-14-3.mol

Synonyms:ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Chemical Property of ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

There total 2 articles about ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate 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: 85.0%

tert-butyldimethylsilyl trifluoroacetate (104410-90-4) + (Z)-ethyl-7-O-benzyl-4,5-O-isopropylidene-2,3-dideoxy-D-ribohept-2-enonate (99409-40-2) → ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate (115828-14-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1021/jo00263a017

Reference yield:

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose (198969-39-0) → ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate (115828-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / CH₂Cl₂ / 4 h / Heating

2: 85 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 0.5 h / 25 °C

With 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1021/jo00263a017

Reference yield: 92.0%

ethyl(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate (115828-14-3) → (Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol (115828-15-4)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo00263a017

upstream raw materials:

tert-butyldimethylsilyl trifluoroacetate

(Z)-ethyl-7-O-benzyl-4,5-O-isopropylidene-2,3-dideoxy-D-ribohept-2-enonate

5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

ethyl(E)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enoate

(Z)-7-O-benzyl-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

(E)-7-O-benzyl-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol