(S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide

Base Information

• Chemical Name: (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide
• CAS No.: 135144-53-5
• Molecular Formula: C₂₈H₄₈N₂O₄Si
• Molecular Weight: 504.786
• Mol file: 135144-53-5.mol

Synonyms:(S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide

Chemical Property of (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide

There total 10 articles about (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide 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:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide (135144-53-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 75 percent / CF₃SO₃H / pentane; CH₂Cl₂

2: lithium aluminum hydride (LAH) / diethyl ether / 0 °C

3: Ph₃P, NBS / CH₂Cl₂ / 0 °C

4: 1. Mg

5: 1. potassium hexamethyldisilazide (KHMDS) / 1. -78 deg C to 0 deg C, 2. -78 deg C

6: silica gel, oxalic acid / CH₂Cl₂

7: diethyl cyanophosphonate (DEPC), TEA

8: pyridine

9: diethyl cyanophosphonate (DEPC), TEA

With pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; diethyl cyanophosphonate; TEA; oxalic acid; silica gel; potassium hexamethylsilazane; magnesium; triphenylphosphine; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo00016a004

Reference yield:

(S)-3-benzyloxy-2-methylpropan-1-ol (63930-46-1) → (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide (135144-53-5)

Guidance literature:

Multi-step reaction with 7 steps

1: Ph₃P, NBS / CH₂Cl₂ / 0 °C

2: 1. Mg

3: 1. potassium hexamethyldisilazide (KHMDS) / 1. -78 deg C to 0 deg C, 2. -78 deg C

4: silica gel, oxalic acid / CH₂Cl₂

5: diethyl cyanophosphonate (DEPC), TEA

6: pyridine

7: diethyl cyanophosphonate (DEPC), TEA

With pyridine; N-Bromosuccinimide; diethyl cyanophosphonate; TEA; oxalic acid; silica gel; potassium hexamethylsilazane; magnesium; triphenylphosphine; In dichloromethane;

DOI:10.1021/jo00016a004

Reference yield:

(2R)-3-bromo-2-[(methylpropyloxy)methyl]benzene (63930-47-2) → (S)-2-Acetylamino-4-methyl-pentanoic acid [(Z)-(1R,4S)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,4-dimethyl-pent-2-enyl]-amide (135144-53-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1. Mg

2: 1. potassium hexamethyldisilazide (KHMDS) / 1. -78 deg C to 0 deg C, 2. -78 deg C

3: silica gel, oxalic acid / CH₂Cl₂

4: diethyl cyanophosphonate (DEPC), TEA

5: pyridine

6: diethyl cyanophosphonate (DEPC), TEA

With pyridine; diethyl cyanophosphonate; TEA; oxalic acid; silica gel; potassium hexamethylsilazane; magnesium; In dichloromethane;

DOI:10.1021/jo00016a004

upstream raw materials:

acetic acid

Fmoc-Leu-OH

(S)-3-benzyloxy-2-methylpropan-1-ol

(2R)-3-bromo-2-[(methylpropyloxy)methyl]benzene

Downstream raw materials:

(S)-2-Acetylamino-4-methyl-pentanoic acid ((1R,4R)-5-benzyloxy-3-fluoro-1,4-dimethyl-2-oxo-pentyl)-amide