Boc-D-Homoserine lactone

Base Information

• Chemical Name: Boc-D-Homoserine lactone
• CAS No.: 67198-86-1
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.222
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID00350875
• Nikkaji Number: J1.247.650G
• Wikidata: Q72503937
• Mol file: 67198-86-1.mol

Synonyms:Boc-D-Homoserine lactone;67198-86-1;Boc-D-Homoserinelactone;tert-butyl N-[(3R)-2-oxooxolan-3-yl]carbamate;(R)-TERT-BUTYL 2-OXOTETRAHYDROFURAN-3-YLCARBAMATE;(R)-2- Boc-amino -|A-butyrolactone;N-Boc-D-homoserine lactone;MFCD09037376;(R)-tert-butyl (2-oxotetrahydrofuran-3-yl)carbamate;tert-butyl (R)-(2-oxotetrahydrofuran-3-yl)carbamate;SCHEMBL1271608;DTXSID00350875;IMWMFJMYEKHYKG-ZCFIWIBFSA-N;FD1148;AKOS005146318;AKOS015841335;Boc-D-Homoserine lactone (Boc-D-Hsl);CS-W022601;AC-23767;DS-13468;A9017;EN300-7108632;tert-Butyl N-[(3R)-2-oxotetrahydrofuran-3-yl]carbamate;(2-oxotetrahydro-furan-3(R)-yl)-carbamic acid tert-butyl ester;(R)-2- Boc-Amino -gamma-Butyrolactone;Boc-D-Homoserine Lactone

Chemical Property of Boc-D-Homoserine lactone

Chemical Property:

• Melting Point: 115-118 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• Boiling Point: 363.7±31.0 °C(Predicted)
• PKA: 11.21±0.20(Predicted)
• PSA: 64.63000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.21750
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

Boc-D-HomoserineLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCOC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CCOC1=O

Technology Process of Boc-D-Homoserine lactone

There total 11 articles about Boc-D-Homoserine lactone 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-α-amino-γ-butyrolactone hydrobromide (110045-70-0) → (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone (67198-86-1,132957-40-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol101584z

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-(+)-α-amino-γ-butyrolactone hydrochloride (104347-13-9) → (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone (67198-86-1,132957-40-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1135/cccc20061199

Reference yield: 67.0%

N-t-butyloxycarbonyl D-homoserine lactone [α] + dicyclohexylamine salt of N-t-butyloxycarbonyl D-methionine (61315-59-1,51537-18-9) + methyl iodide (74-88-4) → (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone (67198-86-1,132957-40-5)

Guidance literature:

With chloro-trimethyl-silane; In tetrahydrofuran; ethyl acetate; acetonitrile;

upstream raw materials:

methyl (2R)-2-[(tert-butoxy)carbonylamino]-5-methyl-5-phenyl-5-silahexanoate

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-4-hydroxybutanoate

di-tert-butyl dicarbonate

(R)-(+)-α-amino-γ-butyrolactone hydrochloride

Downstream raw materials:

(1-(hydroxymethyl)-3-hydroxypropyl)carbamic acid tert-butyl ester

-propoxy>phenyl>glyoxylic acid

(R)-2-tert-Butoxycarbonylamino-4-[4-(4-nitro-benzyloxyoxalyl)-phenoxy]-butyric acid benzhydryl ester

(R)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoic acid

Refernces

• 1、 Martinkova, Miroslava,Gonda, Jozef,Dzoganova, Martina. "A new stereocontrolled approach to a key intermediate in the synthesis of (25,3R)-capreomycidine". . p. 1199 - 1210. Retrieved 2008/03/27.
• 2、 Shikata, Keiji,Niiro, Hayato,Azuma, Hideki,Tachibana, Taro,Ogino, Kenji. "Synthesis of non-natural C2-homo-ceramide and its apoptotic activity against HL-60 cells". . p. 613 - 616. Retrieved 2007/10/03.