(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

Base Information

Chemical Name:(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one
CAS No.:882039-18-1
Molecular Formula:C₄₁H₆₅IO₆Si
Molecular Weight:808.953
Hs Code.:

(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

Synonyms:(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

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Chemical Property of (2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

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Technology Process of (2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

There total 10 articles about (2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-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:

: (2S,3S,4R,8S,10S,11R,12S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-yn-5-one

: 882039-18-1
(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

Guidance literature:: With pyridine; potassium diazodicarboxylate; acetic acid; In methanol; for 6h;
DOI:10.1021/ol052917e

Reference yield:

: (3S,5S,7R)-8-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3,5,7-trimethyl-1-(trimethylsilyl)oct-1-yn-4-ol

: 882039-18-1
(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 70 percent / CF₃SO₃H / diethyl ether / 7 h / cooling

2.1: camphorsulfonic acid / methanol / 2 h / 20 °C

3.1: PhI(OAc)2; TEMPO / CH₂Cl₂ / 1.5 h / 25 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran / 2.5 h / -78 - 20 °C

5.1: hydrochloric acid / acetonitrile; H₂O / 2 h / 20 °C

5.2: 500 mg / NaBH₄ / acetonitrile; H₂O / 3 h / 20 °C

6.1: 80 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 2 h / 20 °C

7.1: tert-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

7.2: 65 percent / diethyl ether; pentane / 0.67 h / cooling

8.1: N-iodosuccinimide; AgNO₃ / dimethylformamide / 2 h / 20 °C

9.1: 360 mg / dipotassium azadicarboxylate; pyridine; acetic acid / methanol / 6 h

With pyridine; 1H-imidazole; hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium diazodicarboxylate; silver nitrate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; pentane; 4.2: Wittig reaction;
DOI:10.1021/ol052917e

Reference yield:

: 882039-22-7
(2R,4S,5R,6S)-2,4,6-trimethyl-5-({[4-(methyloxy)phenyl]methyl}oxy)-8-(trimethylsilyl)oct-7-ynal

: 882039-18-1
(2S,3S,4R,8S,10S,11R,12S,13Z)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 - 20 °C

2.1: hydrochloric acid / acetonitrile; H₂O / 2 h / 20 °C

2.2: 500 mg / NaBH₄ / acetonitrile; H₂O / 3 h / 20 °C

3.1: 80 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 2 h / 20 °C

4.1: tert-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

4.2: 65 percent / diethyl ether; pentane / 0.67 h / cooling

5.1: N-iodosuccinimide; AgNO₃ / dimethylformamide / 2 h / 20 °C

6.1: 360 mg / dipotassium azadicarboxylate; pyridine; acetic acid / methanol / 6 h

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium diazodicarboxylate; silver nitrate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; pentane; 1.2: Wittig reaction;
DOI:10.1021/ol052917e