(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

Base Information

Chemical Name:(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane
CAS No.:364597-39-7
Molecular Formula:C₂₇H₃₉NO₄S
Molecular Weight:473.677
Hs Code.:

Synonyms:(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

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Chemical Property of (2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

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Technology Process of (2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

There total 14 articles about (2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane 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: 94.0%

: 364597-85-3
(2S,3S,4S,6R,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methyl-4-(phenylseleno)undecane

: 364597-39-7
(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 0.75h; Reflux;
DOI:10.1039/c2ob26801a

Reference yield: 94.0%

: N-{(R)-1-[(2R,5S)-5-((S)-2-Benzyloxy-1-methyl-ethyl)-4-phenylselanyl-tetrahydro-furan-2-ylmethyl]-butyl}-4,N-dimethyl-benzenesulfonamide

: 364597-39-7
(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

Guidance literature:: With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile);
DOI:10.1016/S0040-4039(01)00921-2

Reference yield:

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

: 364597-39-7
(2S,3R,6S,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methylundecane

Guidance literature:: Multi-step reaction with 9 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; tri-n-butyl-tin hydride; ammonium formate; tin(IV) chloride; sodium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; 2,2'-azobis(isobutyronitrile); In diethyl ether; 1: conjugate addition / 2: transfer hydrogenolysis / 4: methylation / 5: reduction;
DOI:10.1016/S0040-4039(01)00921-2