(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

Base Information

Chemical Name:(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane
CAS No.:364597-91-1
Molecular Formula:C₃₅H₆₃NO₄Si
Molecular Weight:589.975
Hs Code.:

Synonyms:(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

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Chemical Property of (2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

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Technology Process of (2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

There total 21 articles about (2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane 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: 84.0%

: 364597-55-7
(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,7,9-trimethyloctadecane

: 364597-91-1
(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

Guidance literature:: With Na-naphth; at -60 ℃;
DOI:10.1016/S0040-4039(01)00921-2

Reference yield:

: 85144-28-1
tert-butyl (2E)-hex-2-enoate

: 364597-91-1
(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

Guidance literature:: Multi-step reaction with 19 steps

1: 89 percent / n-BuLi / -78 °C

2: 100 percent / HCO₂NH₄; HCO₂H / Pd(OH)2/C

3: 91 percent / Et₃N; DMAP

4: 100 percent / NaH

5: 94 percent / LiAlH₄ / diethyl ether

6: 95 percent / (COCl)2; DMSO; Et₃N

7: 64 percent / SnCl₄ / -78 °C

8: 43 percent / SnCl₄

9: 94 percent / Bu₃SnH / AIBN

10: 98 percent / H₂ / Pd/C / ethanol

11: 90 percent / (COCl)2; DMSO; Et₃N

12: 63 percent / (i-Pr)2NLi / -78 °C

13: 80 percent / DIBAL-H

14: 95 percent / (COCl)2; DMSO; Et₃N

15: 83 percent / SnCl₄

16: 54 percent / ZnCl₂ / CH₂Cl₂

17: 85 percent / Bu₃SnH / AIBN

18: 84 percent / Na-naphth / -60 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; Na-naphth; hydrogen; tri-n-butyl-tin hydride; ammonium formate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In diethyl ether; ethanol; dichloromethane; 1: conjugate addition / 2: transfer hydrogenolysis / 4: methylation / 5: reduction / 10: hydrogenolysis / 14: reduction;
DOI:10.1016/S0040-4039(01)00921-2

Reference yield:

: 217823-13-7
tert-butyl (3R)-3-aminohexanoate

: 364597-91-1
(2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-methylamino)-2,7,9-trimethyloctadecane

Guidance literature:: Multi-step reaction with 17 steps

1: 91 percent / Et₃N; DMAP

2: 100 percent / NaH

3: 94 percent / LiAlH₄ / diethyl ether

4: 95 percent / (COCl)2; DMSO; Et₃N

5: 64 percent / SnCl₄ / -78 °C

6: 43 percent / SnCl₄

7: 94 percent / Bu₃SnH / AIBN

8: 98 percent / H₂ / Pd/C / ethanol

9: 90 percent / (COCl)2; DMSO; Et₃N

10: 63 percent / (i-Pr)2NLi / -78 °C

11: 80 percent / DIBAL-H

12: 95 percent / (COCl)2; DMSO; Et₃N

13: 83 percent / SnCl₄

14: 54 percent / ZnCl₂ / CH₂Cl₂

15: 85 percent / Bu₃SnH / AIBN

16: 84 percent / Na-naphth / -60 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; Na-naphth; hydrogen; tri-n-butyl-tin hydride; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In diethyl ether; ethanol; dichloromethane; 2: methylation / 3: reduction / 8: hydrogenolysis / 12: reduction;
DOI:10.1016/S0040-4039(01)00921-2