(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

• Chemical Name: (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS No.: 149525-94-0
• Molecular Formula: C₆₄H₇₈O₆Si₂
• Molecular Weight: 999.491

Synonyms:(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property of (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property:

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Technology Process of (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 8 articles about (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 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: 65.0%

(-)-8-phenylmenthyl dimethyl phosphonoacetate (113368-89-1) + meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial → (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (149525-94-0) + (E)-(4S,6S,8R)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester + (2E,9E)-(4S,6S,8R)-6-Benzyloxy-4,8-bis-(tert-butyl-diphenyl-silanyloxy)-undeca-2,9-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Guidance literature:

(-)-8-phenylmenthyl dimethyl phosphonoacetate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial; In tetrahydrofuran; toluene; at -78 ℃;

DOI:10.1021/jo981102z

Reference yield: 65.0%

(-)-8-phenylmenthyl dimethyl phosphonoacetate (113368-89-1) + meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial → (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (149525-94-0)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1080/10426509908546209

Reference yield: 60.0%

meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial + (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (155795-48-5) → (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (149525-94-0) + (E)-(4S,6S,8R)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester + (2E,9E)-(4S,6S,8R)-6-Benzyloxy-4,8-bis-(tert-butyl-diphenyl-silanyloxy)-undeca-2,9-dienedioic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Guidance literature:

(diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial; In tetrahydrofuran; toluene; at -78 ℃;

DOI:10.1021/jo981102z

upstream raw materials:

(-)-8-phenylmenthyl dimethyl phosphonoacetate

(diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

(Diisopropoxy-phosphoryl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

6-(benzyloxy)-1,3-cycloheptadiene

Downstream raw materials:

(E)-(4R,6R,8S)-6-benzyloxy-4,8-dihydroxy-9-(toluene-4-sulfonyloxy)non-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

(E)-(4R,6R,8S)-6-benzyloxy-4,8,9-trihydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

(E)-(4R,6R)-6-Benzyloxy-4-hydroxy-7-(S)-oxiranyl-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

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