(Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid
• CAS No.: 39968-94-0
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686

Synonyms:(Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid

Chemical Property of (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid

Chemical Property:

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Technology Process of (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid

There total 3 articles about (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid 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:

(Z)-7-[(1R,2S,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-hept-5-enoic acid (39968-92-8) → (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid (39968-94-0)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone;

DOI:10.1021/ja00772a043

Reference yield:

(3aR,4S,5R,6aS)-4-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[b]furan-2-one (39968-91-7) → (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid (39968-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1: iBu₂AlH / toluene

3: CrO₃, H₂SO₄ / acetone

With chromium(VI) oxide; sulfuric acid; diisobutylaluminium hydride; In acetone; toluene;

DOI:10.1021/ja00772a043

Reference yield:

(3aR,4S,5R,6aS)-4-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[b]furan-2-ol (41194-67-6,54516-18-6) → (Z)-7-[(1R,2S,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-hept-5-enoic acid (39968-94-0)

Guidance literature:

Multi-step reaction with 2 steps

2: CrO₃, H₂SO₄ / acetone

With chromium(VI) oxide; sulfuric acid; In acetone;

DOI:10.1021/ja00772a043

upstream raw materials:

(Z)-7-[(1R,2S,3R,5S)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-hept-5-enoic acid

(3aR,4S,5R,6aS)-4-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-4-Benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[b]furan-2-ol

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