(S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester
• CAS No.: 613264-80-5
• Molecular Formula: C₂₄H₂₇NO₇
• Molecular Weight: 441.481
• Mol file: 613264-80-5.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester

There total 1 articles about (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) 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: 81.0%

3-bromomethyl-3-methyloxetane (78385-26-9) + Z-Asp-OBn (4779-31-1) → (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester (613264-80-5)

Guidance literature:

Z-Asp-OBn; With CsCO₃; In water; for 2h;

3-bromomethyl-3-methyloxetane; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Further stages.;

DOI:10.1002/ejoc.200300199

Reference yield: 90.0%

(S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester (613264-80-5) → (S)-2-Benzyloxycarbonylamino-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propionic acid benzyl ester (613264-81-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -30 - 20 ℃; for 8h;

DOI:10.1002/ejoc.200300199

Reference yield:

(S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester (613264-80-5) → ((2R,3S)-3-Dibenzylamino-2-ethyl-8-methyl-1,6,10-trioxa-spiro[4.5]dec-8-yl)-methanol

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / BF₃*OEt₂ / CH₂Cl₂ / 8 h / -30 - 20 °C

2: 78 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

3: H₂ / Pd(OH)2/C / methanol / 20 °C

4: 952 mg / K₂CO₃ / acetonitrile / 20 °C

5: 95 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

6: 62 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

With lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 5: Swern oxidation;

DOI:10.1002/ejoc.200300199

upstream raw materials:

3-bromomethyl-3-methyloxetane

Z-Asp-OBn

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propionic acid benzyl ester

(S)-2-Dibenzylamino-3-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propan-1-ol