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

Base Information

Chemical Name:(2S,3S,4S,5R,8S,10S,11R,12S,13Z)-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-ene-3,5-diol
CAS No.:882039-20-5
Molecular Formula:C₃₅H₅₃IO₆
Molecular Weight:696.707
Hs Code.:

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

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

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

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

: 882039-19-2
(2S,3S,4R,8S,10S,11R,12S,13Z)-3-hydroxy-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-en-5-one

: 882039-20-5
(2S,3S,4S,5R,8S,10S,11R,12S,13Z)-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-ene-3,5-diol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 4h;
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

: 882039-20-5
(2S,3S,4S,5R,8S,10S,11R,12S,13Z)-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-ene-3,5-diol

Guidance literature:: Multi-step reaction with 11 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

10.1: 95 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C

11.1: DIBAL-H / tetrahydrofuran / 4 h / -78 °C

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; diisobutylaluminium hydride; pyridine hydrogenfluoride; 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

: 882039-20-5
(2S,3S,4S,5R,8S,10S,11R,12S,13Z)-14-iodo-2,4,8,10,12-pentamethyl-1,11-bis({[4-(methyloxy)phenyl]methyl}oxy)tetradec-13-ene-3,5-diol

Guidance literature:: Multi-step reaction with 8 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

7.1: 95 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: DIBAL-H / tetrahydrofuran / 4 h / -78 °C

With pyridine; 1H-imidazole; hydrogenchloride; N-iodo-succinimide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium diazodicarboxylate; diisobutylaluminium hydride; pyridine hydrogenfluoride; 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