(S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 145147-51-9
• Molecular Formula: C₂₃H₃₂N₂O₇
• Molecular Weight: 448.516

Synonyms:(S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property of (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

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Technology Process of (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 2 articles about (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl 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:

O1,O2-isopropylidene-O5-methanesulfonyl-α-D-xylofuranose (29581-01-9) → (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145147-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol

2: DCC, 4-dimethylaminopyridine (DMAP)

With dmap; dicyclohexyl-carbodiimide; In methanol;

DOI:10.1016/S0040-4039(00)60020-5

Reference yield:

N-allyloxycarbonyl-(S)-phenylalanate (90508-20-6) + 1,2-isopropylidene-5-deoxy-5-N,N-dimethylamino-α-D-xylofuranose (145147-43-9) → (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145147-51-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1016/S0040-4039(00)60020-5

Reference yield: 74.0%

Glycine tert-butyl ester (6456-74-2) + (S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145147-51-9) → Aloc-Phe-Gly-OtBu (145147-65-5)

Guidance literature:

lithium bromide; In dichloromethane; 1.) 20 deg C, 2 d, 2.) 40 deg C, 1 d;

DOI:10.1016/S0040-4039(00)60020-5

upstream raw materials:

N-allyloxycarbonyl-(S)-phenylalanate

1,2-isopropylidene-5-deoxy-5-N,N-dimethylamino-α-D-xylofuranose

O¹,O²-isopropylidene-O⁵-methanesulfonyl-α-D-xylofuranose

Downstream raw materials:

Aloc-Phe-Ala-OtBu

Aloc-Phe-Val-OtBu

Aloc-Phe-Gly-OtBu

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