methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

Base Information

• Chemical Name: methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate
• CAS No.: 132970-32-2
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357
• Mol file: 132970-32-2.mol

Synonyms:methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

Chemical Property of methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

There total 5 articles about methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate 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: 85.0%

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2)

Guidance literature:

With potassium tert-butylate;

DOI:10.1016/0957-4166(96)00038-9

Reference yield:

N-benzyloxycarbonyl-α-(diphenylphosphono)glycine methyl ester (1191124-96-5) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (173327-94-1) + methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2)

Guidance literature:

N-benzyloxycarbonyl-α-(diphenylphosphono)glycine methyl ester; With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h; Inert atmosphere;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; diethyl ether; at 20 ℃; for 16h; Reagent/catalyst; Temperature; Time; Overall yield = 92 %; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201300112

Reference yield:

methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate (114684-69-4) + 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → methyl (4S,2E)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (173327-94-1) + methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2)

Guidance literature:

With sodium periodate; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium carbonate; Yield given. Multistep reaction. Yields of byproduct given; 1.) 1 h, 2.) CH₂Cl₂, RT, 4 h;

DOI:10.1246/bcsj.68.3151

upstream raw materials:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

2,3-isopropylidene-glyceraldehyde

methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate

Downstream raw materials:

ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-(methoxymethoxy)butyl>thiazole-4-carboxylate

ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-dihydroxybutyl>thiazole-4-carboxylate

ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-hydroxy-3-(methoxymethoxy)butyl>thiazole-4-carboxylate

ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-3,4-(isopropylidenedioxy)butyl>thiazole-4-carboxylate