N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

Base Information

Chemical Name:N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide
CAS No.:364597-47-7
Molecular Formula:C₂₃H₃₉NO₅S
Molecular Weight:441.632
Hs Code.:

Synonyms:N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

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Chemical Property of N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

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Technology Process of N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

There total 20 articles about N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide 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: 89.0%

: 364597-87-5
(2R,3R,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecan-1-ol

: 364597-47-7
N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

Guidance literature:: With tetrabutyl ammonium fluoride;
DOI:10.1016/S0040-4039(01)00921-2

Reference yield: 57.0%

: 917-54-4
methyllithium

: 364597-51-3
(2S,3S,4R,5R,8S,10R)-10-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,3;5,8-bis-epoxy-4-methyltridecan-1-ol

: 364597-47-7
N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

Guidance literature:: methyllithium; With copper(l) iodide; In diethyl ether; at -10 ℃; for 0.5h;

(2S,3S,4R,5R,8S,10R)-10-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,3;5,8-bis-epoxy-4-methyltridecan-1-ol; In diethyl ether; at -10 ℃; for 5h;
DOI:10.1039/c2ob26801a

Reference yield:

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

: 364597-47-7
N-{(R)-1-[(2S,5R)-5-((1S,2R,3R)-2,4-Dihydroxy-1,3-dimethyl-butyl)-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 15 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: 89 percent / TBAF

With dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; ammonium formate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In diethyl ether; ethanol; 1: conjugate addition / 2: transfer hydrogenolysis / 4: methylation / 5: reduction / 10: hydrogenolysis / 14: reduction / 15: deprotection;
DOI:10.1016/S0040-4039(01)00921-2