Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide

Base Information

• Chemical Name: Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide
• CAS No.: 184951-89-1
• Molecular Formula: C21H23 N5 O5 S
• Molecular Weight: 457.5
• DSSTox Substance ID: DTXSID90472959
• Nikkaji Number: J806.056H
• Wikidata: Q72494411
• Mol file: 184951-89-1.mol

Synonyms:184951-89-1;Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide;tert-butyl N-[(2S)-1-(6-nitrobenzotriazol-1-yl)-3-phenylmethoxy-1-sulfanylidenepropan-2-yl]carbamate;(Boc-L-2-amino-3-benzyloxypropanethioic acid-1-(6-nitro)benzotriazolide);(s)-2-(boc-amino)-3-benzyloxy-propanethioic o-acid;DTXSID90472959;MFCD01318727;A18358;(S)-tert-Butyl (3-(benzyloxy)-1-(6-nitro-1H-benzo[d][1,2,3]triazol-1-yl)-1-thioxopropan-2-yl)carbamate;(S)-tert-butyl 3-(benzyloxy)-1-(6-nitro-1H-benzo[d][1,2,3]triazol-1-yl)-1-thioxopropan-2-ylcarbamate;(S)-tert-Butyl(3-(benzyloxy)-1-(6-nitro-1H-benzo[d][1,2,3]triazol-1-yl)-1-thioxopropan-2-yl)carbamate;1-[(S)-1-Thioxo-2-[(tert-butyloxycarbonyl)amino]-3-(benzyloxy)propyl]-6-nitro-1H-benzotriazole;Carbamic acid,[2-(6-nitro-1H-benzotriazol-1-yl)-1-[(phenylmethoxy)methyl]-2-thioxoethyl]-,1,1-dimethylethyl ester,(S)-(9ci);tert-Butyl [(2S)-3-(benzyloxy)-1-(6-nitro-1H-benzotriazol-1-yl)-1-sulfanylidenepropan-2-yl]carbamate

Chemical Property of Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide

Chemical Property:

• PKA: 9.57±0.46(Predicted)
• PSA: 156.18000
• Density: 1.35
• LogP: 4.53920
• Storage Temp.: -15°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 457.14199002
• Heavy Atom Count: 32
• Complexity: 677

Purity/Quality:

97% ^*data from raw suppliers

Boc-Thionoser(Bzl)-1-(6-nitro)benzotriazolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(COCC1=CC=CC=C1)C(=S)N2C3=C(C=CC(=C3)[N+](=O)[O-])N=N2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](COCC1=CC=CC=C1)C(=S)N2C3=C(C=CC(=C3)[N+](=O)[O-])N=N2

Technology Process of Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide

There total 4 articles about Boc-ThionoSer(Bzl)-1-(6-nitro)benzotriazolide 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: 83.0%

[(S)-1-(2-Amino-5-nitro-phenylthiocarbamoyl)-2-benzyloxy-ethyl]-carbamic acid tert-butyl ester (184951-82-4) → [(S)-1-Benzyloxymethyl-2-(6-nitro-benzotriazol-1-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (184951-89-1)

Guidance literature:

With sodium nitrite; In water; acetic acid; at 0 ℃; for 0.5h;

DOI:10.1021/jo961245q

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) → [(S)-1-Benzyloxymethyl-2-(6-nitro-benzotriazol-1-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (184951-89-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate / 1) THF, -20 deg C, 10 min; 2) THF, -15 deg C, 2 h, rt, overnight

2: 84 percent / P₄S₁₀, Na₂CO₃ / tetrahydrofuran / 1) 0 deg C, 30 min, 2.) rt, 2.5 h

3: 83 percent / NaNO₂ / acetic acid; H₂O / 0.5 h / 0 °C

With 4-methyl-morpholine; tetraphosphorus decasulfide; sodium carbonate; sodium nitrite; isobutyl chloroformate; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/jo961245q

Reference yield:

4-Nitrophenylene-1,2-diamine (99-56-9) → [(S)-1-Benzyloxymethyl-2-(6-nitro-benzotriazol-1-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (184951-89-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate / 1) THF, -20 deg C, 10 min; 2) THF, -15 deg C, 2 h, rt, overnight

2: 84 percent / P₄S₁₀, Na₂CO₃ / tetrahydrofuran / 1) 0 deg C, 30 min, 2.) rt, 2.5 h

3: 83 percent / NaNO₂ / acetic acid; H₂O / 0.5 h / 0 °C

With 4-methyl-morpholine; tetraphosphorus decasulfide; sodium carbonate; sodium nitrite; isobutyl chloroformate; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/jo961245q

upstream raw materials:

[(S)-1-(2-Amino-5-nitro-phenylthiocarbamoyl)-2-benzyloxy-ethyl]-carbamic acid tert-butyl ester

BOC-O-benzyl-L-serine

4-Nitrophenylene-1,2-diamine

[(S)-1-(2-Amino-5-nitro-phenylcarbamoyl)-2-benzyloxy-ethyl]-carbamic acid tert-butyl ester