(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

Base Information

Chemical Name:(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol
CAS No.:1257329-36-4
Molecular Formula:C₃₉H₇₃IO₅Si₂
Molecular Weight:805.081
Hs Code.:

Synonyms:(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

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Chemical Property of (2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

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Technology Process of (2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

There total 15 articles about (2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol 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: 80.0%

: 1257329-34-2
(5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S,Z)-4-iodobut-3-en-2-yl]-13-[(4-methoxybenzyl)oxy]-2,2,3,3,6,8,12,14,17,17,18,18-dodecamethyl-4,16-dioxa-3,17-disilanonadecane

: 1257329-36-4
(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

Guidance literature:: With pyridine; pyridine hydrofluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201001018

Reference yield:

: 143236-77-5
[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol

: 1257329-36-4
(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

Guidance literature:: Multi-step reaction with 16 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

3.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

5.2: 1.08 h / -78 - 0 °C / Inert atmosphere

6.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

8.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

9.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

10.1: hydrogen / ethanol

11.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

12.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

13.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

14.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

14.2: 1 h / -50 - 20 °C / Inert atmosphere

15.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

16.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; ammonium cerium (IV) nitrate; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; water; hydrogen; diethylzinc; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol; acetonitrile; benzene; 3.1: Dess-Martin oxidation / 4.1: Shioiri alkynylation / 4.2: Shioiri alkynylation / 12.1: Marshall-Tamaru addition;
DOI:10.1002/ejoc.201100244

Reference yield:

: 169105-67-3
(2R,4S)-5-(benzyloxy)-2,4-dimethylpentan-1-ol

: 1257329-36-4
(2S,3S,4R,5R,8S,10S,11R,12S,Z)-5,11-bis(tert-butyldimethylsilyloxy)-14-iodo-3-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyltetradec-13-en-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

3.2: 1.08 h / -78 - 0 °C / Inert atmosphere

4.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / isopropyl alcohol / 5 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

6.1: Wilkinson's catalyst; hydrogen / benzene / 3000.3 Torr

7.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

8.1: hydrogen / ethanol

9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Inert atmosphere

10.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

11.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

12.1: n-butyllithium / hexane / 1 h / -50 °C / Inert atmosphere

12.2: 1 h / -50 - 20 °C / Inert atmosphere

13.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

14.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; Wilkinson's catalyst; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; tetrapropylammonium perruthennate; 2-nitrobenzenesulfonyl hydrazide; hydrogen; diethylzinc; palladium diacetate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol; benzene; 1.1: Dess-Martin oxidation / 2.1: Shioiri alkynylation / 2.2: Shioiri alkynylation / 10.1: Marshall-Tamaru addition;
DOI:10.1002/ejoc.201100244