(Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester
• CAS No.: 85235-30-9
• Molecular Formula: C₄₄H₇₀O₈Si
• Molecular Weight: 755.12

Synonyms:(Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester

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Technology Process of (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester

There total 3 articles about (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester 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:

3,4-dihydro-2H-pyran (110-87-2) + (Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-cyclopentyl}-hept-5-enoic acid (85235-24-1) → (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester (85235-30-9)

Guidance literature:

With pyridine hydrochloride; In dichloromethane; at 25 ℃; for 48h;

DOI:10.1021/jm00360a003

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester (85235-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) HMPA, 70 deg C, 3 h, 2.) HMPA, THF, 10-15 deg C, 1.5 h

2: pyridine hydrochloride / CH₂Cl₂ / 48 h / 25 °C

With pyridine hydrochloride; sodium hydride; In dichloromethane;

DOI:10.1021/jm00360a003

Reference yield:

(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol (85235-23-0) → (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid tetrahydro-pyran-2-yl ester (85235-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) HMPA, 70 deg C, 3 h, 2.) HMPA, THF, 10-15 deg C, 1.5 h

2: pyridine hydrochloride / CH₂Cl₂ / 48 h / 25 °C

With pyridine hydrochloride; sodium hydride; In dichloromethane;

DOI:10.1021/jm00360a003

upstream raw materials:

3,4-dihydro-2H-pyran

(Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-cyclopentyl}-hept-5-enoic acid

(4-carboxybutyl)triphenylphosphonium bromide

(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

17-phenyl-18,19,20-trinor-PGF_2α 9,15-bis(tetrahydropyranyl ether)

(Z)-7-[(1R,2R,5S)-3-Oxo-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

17-phenyl-18,19,20-trinor-PGD₂

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