(5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate

Base Information

• Chemical Name: (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate
• CAS No.: 1236109-32-2
• Molecular Formula: C₃₆H₅₄O₅Si
• Molecular Weight: 594.907

Synonyms:(5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate

Chemical Property of (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate

Chemical Property:

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Technology Process of (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate

There total 1 articles about (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-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: 90.0%

(Z)-7-((1R,2S,3R,5S)-3-(benzyloxy)-5-hydroxy-2-(((triisopropylsilyl)oxy)methyl)cyclopentyl)-5-heptenoic acid (1236109-31-1) + benzyl bromide (100-39-0) → (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate (1236109-32-2)

Guidance literature:

With diisopropylamine; In dichloromethane; at 20 ℃; Product distribution / selectivity;

Reference yield: 100.0%

3,4-dihydro-2H-pyran (110-87-2) + (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate (1236109-32-2) → benzyl (2)-7-[(1R,2S,3R,5S)-2-(triisopropylsilyloxymethyl)-3-(2-phenylmethoxy)-5-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptanoate (1236109-33-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 25 ℃; for 7.5h;

Reference yield:

(5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-[(triisopropylsilyloxy)methyl]cyclopentyl]hept-5-enoate (1236109-32-2) → (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-(hydroxymethyl)cyclopentyl]hept-5-enoate (1236109-38-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

upstream raw materials:

(Z)-7-((1R,2S,3R,5S)-3-(benzyloxy)-5-hydroxy-2-(((triisopropylsilyl)oxy)methyl)cyclopentyl)-5-heptenoic acid

benzyl bromide

Downstream raw materials:

benzyl ⁽²⁾-7-[(1R,2S,3R,5S)-2-(triisopropylsilyloxymethyl)-3-(2-phenylmethoxy)-5-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptanoate

(5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-(hydroxymethyl)cyclopentyl]hept-5-enoate

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