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

Base Information

Chemical Name:(2S,3S,4S,6R,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methyl-4-(phenylseleno)undecane
CAS No.:364597-85-3
Molecular Formula:C₃₃H₄₃NO₄SSe
Molecular Weight:628.735
Hs Code.:

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

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

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

There total 12 articles about (2S,3S,4S,6R,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methyl-4-(phenylseleno)undecane 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: 42.0%

: 5707-04-0
Phenylselenyl chloride

: 364597-37-5
(2R,6S,8R,3Z)-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-1-benzyloxy-2-methylundec-3-en-6-ol

: 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

Guidance literature:: With tin(IV) chloride; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1039/c2ob26801a

Reference yield:

: 364597-53-5
(2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanal

: 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

Guidance literature:: Multi-step reaction with 2 steps

1.1: tin(IV) chloride / dichloromethane / 0.08 h / -78 °C

1.2: 0.83 h / -78 °C

2.1: tin(IV) chloride / dichloromethane / 6 h / 20 °C

With tin(IV) chloride; In dichloromethane;
DOI:10.1039/c2ob26801a

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 2 h / -78 °C

2.1: 20% palladium hydroxide-activated charcoal; ammonium formate; formic acid / methanol / 3 h / 20 °C

3.1: triethylamine; dmap / dichloromethane / 24 h / 0 - 20 °C

4.1: sodium hydride / tetrahydrofuran / 2 h / 20 °C

4.2: 15 h / 20 °C

5.1: lithium aluminium tetrahydride / diethyl ether / 1.5 h / 0 - 20 °C

6.1: oxalyl dichloride; triethylamine; dimethyl sulfoxide / dichloromethane / 2 h / -78 - 20 °C

7.1: tin(IV) chloride / dichloromethane / 0.08 h / -78 °C

7.2: 0.83 h / -78 °C

8.1: tin(IV) chloride / dichloromethane / 6 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; 20% palladium hydroxide-activated charcoal; ammonium formate; tin(IV) chloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1039/c2ob26801a