(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

Base Information

• Chemical Name: (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate
• CAS No.: 128971-86-8
• Molecular Formula: C₃₄H₃₇NO₅Si
• Molecular Weight: 567.757
• Mol file: 128971-86-8.mol

Synonyms:(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

Chemical Property of (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

There total 4 articles about (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate 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: 89.0%

(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-84-6) → (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-86-8)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 60 ℃; for 18h;

DOI:10.1021/jo00304a024

Reference yield:

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4) → (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) SOCl₂, Et₃N, 2) RuCl₃*3H₂O, NaIO₄ / 1) CH₂Cl₂, room temp., 1 h, 2) MeCN, H₂O, room temp., 60 min.

2: 1) NaN₃, 2) 20 percent aq. H₂SO₄ / 1) acetone, H₂O, room temp., 1 h, 2) Et₂O, room temp., 16 h

3: 82 percent / i-Pr₂NEt, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 18 h / Ambient temperature

4: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

With dmap; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00304a024

Reference yield:

(2S,3R)-Dibenzyl 2-Azido-3-hydroxysuccinate (128971-83-5) → (2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / i-Pr₂NEt, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 18 h / Ambient temperature

2: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

With dmap; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00304a024

upstream raw materials:

(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate

(2S,3R)-Dibenzyl 2-Azido-3-hydroxysuccinate

(4R,5R)-Dibenzyl 1,3,2-Dioxathiolane-4,5-dicarboxylate 2,2-Dioxide

Downstream raw materials:

(3R,4S)-Benzyl 3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylate

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<<4-(benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-2-azetidinone

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<<4-(benzyloxy)-3-hydroxy-2-methyl-4-nitro-2-butyl>thio>-2-azetidinone

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-oxo-2-propyl)thio>-2-azetidinone