(E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Base Information

• Chemical Name: (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one
• CAS No.: 1030835-90-5
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:(E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

Chemical Property of (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

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Technology Process of (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

There total 2 articles about (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-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: 82.0%

4-[(2-methoxyethoxy)methoxy]hex-5-en-2-yl 3,4-bis(benzyloxy)hex-5-enoate → (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (1030835-90-5)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; for 14h; Reflux;

DOI:10.1002/ejoc.200700868

Reference yield: 32.0%

(3S,4S,7S,9R,E)-3,4-bis(benzyloxy)-9-hydroxy-7-[(2-methoxyethoxy)methoxy]dec-5-enoic acid (1030835-88-1) → (E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (1030835-90-5)

Guidance literature:

(3S,4S,7S,9R,E)-3,4-bis(benzyloxy)-9-hydroxy-7-[(2-methoxyethoxy)methoxy]dec-5-enoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With dmap; In benzene; at 80 ℃; for 2h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.200700868

Reference yield: 78.0%

(E)-4,5-bis(benzyloxy)-8-[(2-methoxyethoxy)methoxy]-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (1030835-90-5) → (4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one (127393-89-9,147705-04-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.200700868

upstream raw materials:

(3S,4S,7S,9R,E)-3,4-bis(benzyloxy)-9-hydroxy-7-[(2-methoxyethoxy)methoxy]dec-5-enoic acid

Downstream raw materials:

(4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-4,5,9,10-tetrahydro-3H-oxecin-2(8H)-one

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