(2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol

Base Information

• Chemical Name: (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol
• CAS No.: 141438-62-2
• Molecular Formula: C₂₇H₃₇NO₆Si
• Molecular Weight: 499.679

Synonyms:(2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol

Chemical Property of (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol

There total 8 articles about (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol 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:

Benzoic acid (1R,2R,3R)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-1-vinyl-butyl ester → (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol (141438-62-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; at 0 ℃; for 0.25h; Yield given;

DOI:10.1021/jo00039a044

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol (141438-62-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / camphorsulfonic acid / dimethylformamide / 90 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 24 °C

3: 72 percent / N-bromosuccinimide, BaCO₃, azobis(isobutyronitrile) / CCl₄ / 3 h / Heating

4: 100 percent / NaI / acetone / 5 h / Heating

5: activated Zn / ethanol; H₂O / 1 h / Heating

6: NaBH₄ / ethanol; H₂O / 0.25 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; barium carbonate; sodium iodide; zinc; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00039a044

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4R)-2--4-(benzoyloxy)-3-<(tert-butyldimethylsilyl)oxy>-5-hexen-1-ol (141438-62-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 24 °C

2: 72 percent / N-bromosuccinimide, BaCO₃, azobis(isobutyronitrile) / CCl₄ / 3 h / Heating

3: 100 percent / NaI / acetone / 5 h / Heating

4: activated Zn / ethanol; H₂O / 1 h / Heating

5: NaBH₄ / ethanol; H₂O / 0.25 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate; sodium iodide; zinc; In tetrachloromethane; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jo00039a044

upstream raw materials:

benzaldehyde dimethyl acetal

t-butyldimethylsiyl triflate

[(4aR,6S,7R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

methyl 2--4-O-benzoyl-6-bromo-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-D-glucopyranoside

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