(3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene

Base Information

• Chemical Name: (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene
• CAS No.: 120476-96-2
• Molecular Formula: C₂₁H₃₉NO₅
• Molecular Weight: 385.544
• Mol file: 120476-96-2.mol

Synonyms:(3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene

Chemical Property of (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene

There total 1 articles about (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene 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:

2-bromo-3,3-diethoxypropene (17592-40-4) + (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → (3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene + (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene (120476-96-2)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, hexane, -78 deg C, 1 h, 2) THF, -78 deg C, 1 h;

DOI:10.1021/jm00126a038

Reference yield: 100.0%

(3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene (120476-96-2) → (4S,5S)-4-(cyclohexylmethyl)-5-(3',3'-diethoxy-2'-propenyl)oxazolidin-2-one (120476-98-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00126a038

Reference yield:

(3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene (120476-96-2) → (3S,4S)-4-Amino-2-azidomethyl-5-cyclohexyl-pent-1-en-3-ol

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / NaH / dimethylformamide / Ambient temperature

2: 10percent aq. oxalic acid / CH₂Cl₂ / 1 h

3: NaBH₄ / CH₂Cl₂; methanol / 1 h / 0 °C

4: 86 percent / diisopropylethylamine / CH₂Cl₂ / 0.5 h / -10 °C

5: 90 percent / NaN₃ / dimethylformamide / 12 h / 55 °C

6: Ba(OH)2*8H₂O / H₂O; dioxane / Heating

With barium dihydroxide; sodium tetrahydroborate; sodium azide; oxalic acid; sodium hydride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00126a038

upstream raw materials:

2-bromo-3,3-diethoxypropene

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

Downstream raw materials:

(4S,5S)-4-(cyclohexylmethyl)-5-(3',3'-diethoxy-2'-propenyl)oxazolidin-2-one

2-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-propenal

(4S,5S)-4-(cyclohexylmethyl)-5-(3'-hydroxy-2'-propenyl)oxazolidin-2-one

(4S,5S)-4-(cyclohexylmethyl)-5-<3'-azido-2'-propenyl>oxazolidin-2-one