2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

Base Information

Chemical Name:2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate
CAS No.:364597-44-4
Molecular Formula:C₃₇H₅₉NO₆SSi
Molecular Weight:674.03
Hs Code.:

2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

Synonyms:2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

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Chemical Property of 2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

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Technology Process of 2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

There total 14 articles about 2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate 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: 66.0%

: 2,6-dimethylphenyl (2RS,3RS,4S,5R,8S,10R)-2,4-dimethyl-5,8-epoxy-3-hydroxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 364597-44-4
2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

: 2,6-dimethylphenyl (2R,3R,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1039/c2ob26801a

Reference yield: 17.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: (S)-3-Hydroxy-2-methyl-4-((2R,5S)-5-{(R)-2-[methyl-(toluene-4-sulfonyl)-amino]-pentyl}-tetrahydro-furan-2-yl)-pentanoic acid 2,6-dimethyl-phenyl ester

: 364597-44-4
2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

: 2,6-dimethylphenyl (2R,3R,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

Guidance literature:: DOI:10.1016/S0040-4039(01)00921-2

Reference yield:

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

: 364597-44-4
2,6-dimethylphenyl (2S,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate

Guidance literature:: Multi-step reaction with 13 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; hydrogen; tri-n-butyl-tin hydride; ammonium formate; tin(IV) chloride; sodium 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;
DOI:10.1016/S0040-4039(01)00921-2