(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester
• CAS No.: 203919-91-9
• Molecular Formula: C₃₁H₄₈N₂O₁₀Si
• Molecular Weight: 636.815
• Mol file: 203919-91-9.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester

There total 6 articles about (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester 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: 88.0%

N-(tert-butoxycarbonyl)-D-allylglycine (170899-08-8) + (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-(3-hydroxy-propyl) ester 5-(2-trimethylsilanyl-ethyl) ester (203919-90-8) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester (203919-91-9)

Guidance literature:

With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; In dichloromethane; for 16h; Heating;

DOI:10.1021/jo972133h

Reference yield:

D-allylglycine (54594-06-8) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester (203919-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / NaHCO₃ / dioxane; H₂O / 5 h

2: 88 percent / DCC, DMAP, DMAP*HCl / CH₂Cl₂ / 16 h / Heating

With dmap; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jo972133h

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester (203919-91-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / Et₃N, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 10 h

2: 1) n-BuLi / 1) THF, room temperature, 10 min, 2) THF, 12 h

3: 88 percent / DCC, DMAP, DMAP*HCl / CH₂Cl₂ / 16 h / Heating

With dmap; n-butyllithium; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 4-(dimethylamino)pyridine hydrochloride; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo972133h

upstream raw materials:

N-(tert-butoxycarbonyl)-D-allylglycine

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-(3-hydroxy-propyl) ester 5-(2-trimethylsilanyl-ethyl) ester

D-allylglycine

2-(Trimethylsilyl)ethanol

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester