(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

Base Information

Chemical Name:(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol
CAS No.:115828-17-6
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

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Technology Process of (Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

There total 6 articles about (Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol 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: 93.0%

: 115828-16-5
(Z)-7-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-chloro-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

: 115828-17-6
(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at 25 ℃; for 6h;
DOI:10.1021/jo00263a017

Reference yield:

: 198969-39-0
5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

: 115828-17-6
(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / CH₂Cl₂ / 4 h / Heating

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

3: 92 percent / DIBAL / diethyl ether / 1 h / 0 °C

4: 64 percent / methanesulfonyl chloride, 2,4,6-trimethylpyridine, lithium chloride / N,N-dimethyl-acetamide / 2 h / 0 °C

5: 93 percent / LiBEt₃H / tetrahydrofuran / 6 h / 25 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; diisobutylaluminium hydride; lithium triethylborohydride; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl acetamide;
DOI:10.1021/jo00263a017

Reference yield:

: 104410-90-4
tert-butyldimethylsilyl trifluoroacetate

: 115828-17-6
(Z)-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2,3-trideoxy-4,5-O-isopropylidene-D-ribo-hept-2-enitol

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 0.5 h / 25 °C

2: 92 percent / DIBAL / diethyl ether / 1 h / 0 °C

3: 64 percent / methanesulfonyl chloride, 2,4,6-trimethylpyridine, lithium chloride / N,N-dimethyl-acetamide / 2 h / 0 °C

4: 93 percent / LiBEt₃H / tetrahydrofuran / 6 h / 25 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; diisobutylaluminium hydride; lithium triethylborohydride; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl acetamide;
DOI:10.1021/jo00263a017