(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-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-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
CAS No.:149525-95-1
Molecular Formula:C₆₄H₈₀O₆Si₂
Molecular Weight:1001.51
Hs Code.:

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

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

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

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

There total 7 articles about (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-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:

: 113368-89-1
(-)-8-phenylmenthyl dimethyl phosphonoacetate

: meso-(2R,4s,6S)-4-(benzyloxy)-2,6-bis((tert-butyldiphenylsilyl)oxy)heptanedial

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

: 149525-95-1
(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: With sodium tetrahydroborate; 18-crown-6 ether; potassium hexamethylsilazane; Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C, 4 h, 2) MeOH;
DOI:10.1021/jo00067a010

Reference yield:

: meso-(1RS,2SR,3R,5s,7S)-5-(benzyloxy)-3,7-bis((tert-butyldiphenylsilyl)oxy)cycloheptane-1,2-diol

: 149525-95-1
(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / H₅IO₆ / tetrahydrofuran / 2.5 h / 20 °C

2.1: 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: tetrahydrofuran; toluene / -78 °C

2.3: NaBH₄ / 0 °C

With 18-crown-6 ether; potassium hexamethylsilazane; periodic acid; In tetrahydrofuran; toluene; 1.1: Oxidation / 2.1: Metallation / 2.2: Horner-Wadsworth-Emmons reaction / 2.3: Reduction;
DOI:10.1021/jo981102z

Reference yield:

: 113368-89-1
(-)-8-phenylmenthyl dimethyl phosphonoacetate

: 149525-95-1
(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / KHMDS; 18-C-6 / tetrahydrofuran / -78 °C

2: NaBH₄

With sodium tetrahydroborate; 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; 1: Horner-Wadsworth-Emmons reaction / 2: Reduction;
DOI:10.1080/10426509908546209