(E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one

Base Information

• Chemical Name: (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one
• CAS No.: 553665-17-1
• Molecular Formula: C₃₄H₄₈O₇
• Molecular Weight: 568.751

Synonyms:(E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one

Chemical Property of (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one

Chemical Property:

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Technology Process of (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one

There total 35 articles about (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one 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: 67.0%

(4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid (1S,2S)-1-allyl-2-(2-methoxy-ethoxymethoxy)-octyl ester (553665-15-9) → (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one (553665-17-1)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; for 28h; Heating;

DOI:10.1016/S0040-4039(03)00441-6

Reference yield:

(4S,5S)-5-(2-Methoxy-ethoxymethoxy)-undec-1-en-4-ol (553664-96-3) → (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one (553665-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: (PCy₃)2Ru(Cl)2=CHPh / CH₂Cl₂ / 28 h / Heating

With dmap; dicyclohexyl-carbodiimide; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1016/j.tetlet.2005.06.070

Reference yield:

(4R,5R)-4,5-bis(benzyloxy)hept-6-enoic acid (553664-97-4) → (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one (553665-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: (PCy₃)2Ru(Cl)2=CHPh / CH₂Cl₂ / 28 h / Heating

With dmap; dicyclohexyl-carbodiimide; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1016/j.tetlet.2005.06.070

upstream raw materials:

(4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid (1S,2S)-1-allyl-2-(2-methoxy-ethoxymethoxy)-octyl ester

tert-Butyl-((S)-(S)-1-oxiranyl-but-3-enyloxy)-diphenyl-silane

3-(tert-butyl-diphenyl-silanyloxy)-hex-5-ene-1,2-diol

(4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid ethyl ester

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