(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

Base Information

• Chemical Name: (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
• CAS No.: 1257329-34-2
• Molecular Formula: C₄₅H₈₇IO₅Si₃
• Molecular Weight: 919.344

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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: 92.0%

(5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S)-4-iodobut-3-yn-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 (1257329-32-0) → (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 (1257329-34-2)

Guidance literature:

With 2-nitrobenzenesulfonyl hydrazide; triethylamine; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 24h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201001018

Reference yield:

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol (143236-77-5) → (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 (1257329-34-2)

Guidance literature:

Multi-step reaction with 15 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

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; 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:

(2R,4S)-5-(benzyloxy)-2,4-dimethylpentan-1-ol (169105-67-3) → (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 (1257329-34-2)

Guidance literature:

Multi-step reaction with 13 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

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; 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

upstream raw materials:

(5R,6S,8S,11R,12R,13S,14S)-11-(tert-butyldimethylsilyloxy)-5-[(S)-4-iodobut-3-yn-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

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene

(2S,4S,7R,8R,9S,10S)-7,11-bis(tert-butyldimethylsilanyloxy)-9-(4-methoxybenzyloxy)-2,4,8,10-tetramethylundecanal

Downstream raw materials:

(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

(5R,6S,8S,11R)-5-((S,Z)-4-iodobut-3-en-2-yl)-11-((2R,3S,4S,Z)-3-(4-methoxybenzyloxy)-4-methylocta-5,7-dien-2-yl)-2,2,3,3,6,8,13,13,14,14-decamethyl-4,12-dioxa-3,13-disilapentadecane

(2R,3R,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-al

(2Z,4E,6R,7S,9R,10Z,12S,13R,14S,16S,19R,20R,21S,22S,23Z)-methyl 7,13,19-tris(tert-butyldimethylsilyloxy)-9-hydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

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