cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene

Base Information

• Chemical Name: cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene
• CAS No.: 104882-08-8
• Molecular Formula: C₁₉H₃₅NO₂
• Molecular Weight: 309.492

Synonyms:cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene

Chemical Property of cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene

Chemical Property:

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Technology Process of cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene

There total 3 articles about cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene 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:

methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate (98105-41-0) → cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene (104882-08-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAH / toluene / 0.33 h / -78 °C

2: 1.) potassium hydride, 1,1,1,3,3,3-hexamethyldisilazane / 1.) toluene, THF, DMSO, -78 deg C, 1 h, 2.) -78 deg C, 15 min; -78 deg C -> room temperature; 40 deg C, 12 h

With potassium hydride; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In toluene;

DOI:10.1021/jm00120a005

Reference yield:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) + isoamyltriphenylphosphonium bromide (28322-40-9) → cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene (104882-08-8) + trans-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene (104882-09-9)

Guidance literature:

With potassium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) toluene, THF, DMSO, -78 deg C, 1 h, 2.) -78 deg C, 15 min; -78 deg C -> room temperature; 40 deg C, 12 h;

DOI:10.1021/jm00120a005

Reference yield:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) + isoamyltriphenylphosphonium bromide (28322-40-9) → cis-(2S)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-6-methylhept-3-ene (104882-08-8)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction; 1.) THF, -10 deg C, 6 h, 2.) THF, 0 deg C, 0.5 h;

DOI:10.1016/0957-4166(94)80024-3

upstream raw materials:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

isoamyltriphenylphosphonium bromide

methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate

Downstream raw materials:

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(2S,3S,4R)-2<(tert-butyloxycarbonyl)amino>-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(Z)-(S)-1-Cyclohexylmethyl-5-methyl-hex-2-enylamine

((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-carbamic acid ethyl ester

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