(5S,6S,8S,11R)-5-[(R,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

Base Information

• Chemical Name: (5S,6S,8S,11R)-5-[(R,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
• CAS No.: 1309460-58-9
• Molecular Formula: C₄₂H₇₅IO₄Si₂
• Molecular Weight: 827.131
• Mol file: 1309460-58-9.mol

Synonyms:(5S,6S,8S,11R)-5-[(R,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

Chemical Property of (5S,6S,8S,11R)-5-[(R,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,8S,11R)-5-[(R,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

There total 20 articles about (5S,6S,8S,11R)-5-[(R,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 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:

C45H85IO5Si3 → (5S,6S,8S,11R)-5-[(R,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 (1309460-58-9)

Guidance literature:

With potassium hydroxide; In methanol; water; at 0 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201100244

Reference yield:

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide (922523-34-0) → (5S,6S,8S,11R)-5-[(R,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 (1309460-58-9)

Guidance literature:

Multi-step reaction with 20 steps

1.1: ammonia borane / tetrahydrofuran / Inert atmosphere

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

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

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

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

5.2: -78 - 20 °C / Inert atmosphere

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

6.2: 1.08 h / -78 - 0 °C / Inert atmosphere

7.1: (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

8.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

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

10.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

11.1: hydrogen / ethanol

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

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

14.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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

15.2: 1 h / -50 - 20 °C / Inert atmosphere

16.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

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

18.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

19.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

20.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; 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; ammonia borane; 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; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; acetonitrile; benzene; 4.1: Dess-Martin oxidation / 5.1: Shioiri alkynylation / 5.2: Shioiri alkynylation / 13.1: Marshall-Tamaru addition / 18.1: Dess-Martin oxidation / 19.1: Nozaki-Hiyama-Kishi coupling / 20.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

Reference yield:

(2R,4S)-5-benzyloxy-2,4-dimethylpentanal → (5S,6S,8S,11R)-5-[(R,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 (1309460-58-9)

Guidance literature:

Multi-step reaction with 16 steps

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

1.2: -78 - 20 °C / Inert atmosphere

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

2.2: 1.08 h / -78 - 0 °C / Inert atmosphere

3.1: (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

4.1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere

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

6.1: 2,6-dimethylpyridine / dichloromethane / Inert atmosphere

7.1: hydrogen / ethanol

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

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

10.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

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

11.2: 1 h / -50 - 20 °C / Inert atmosphere

12.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 24 h / 20 °C / Inert atmosphere

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

14.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

15.1: chromium dichloride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: potassium hydroxide / methanol; water / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; 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; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; benzene; 1.1: Shioiri alkynylation / 1.2: Shioiri alkynylation / 9.1: Marshall-Tamaru addition / 14.1: Dess-Martin oxidation / 15.1: Nozaki-Hiyama-Kishi coupling / 16.1: Peterson olefination;

DOI:10.1002/ejoc.201100244

upstream raw materials:

(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

(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

Downstream raw materials:

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

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

(R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

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