Z-D-Ser(tbu)-ome

Base Information

• Chemical Name: Z-D-Ser(tbu)-ome
• CAS No.: 93204-37-6
• Molecular Formula: C16H23 N O5
• Molecular Weight: 309.362
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80427175
• Wikidata: Q82239879
• Mol file: 93204-37-6.mol

Synonyms:Z-D-SER(TBU)-OME;93204-37-6;methyl (2R)-3-[(2-methylpropan-2-yl)oxy]-2-(phenylmethoxycarbonylamino)propanoate;Z-O-tert-butyl-D-serine methyl ester;SCHEMBL344382;(R)-methyl 2-(benzyloxycarbonylamino)-3-t-butoxypropanoate;DTXSID80427175;UMAXPCYVVRYQNO-CYBMUJFWSA-N;Z-O-t-Butyl-D-serine methyl ester;MFCD00237366;AKOS025289415;AS-63004;F11087;Methyl N-[(benzyloxy)carbonyl]-O-tert-butyl-D-serinate;(R)-methyl 2-(benzyloxycarbonylamino)-3-tert-butoxypropanoate;D-Serine,o-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-,methyl ester;METHYL (2R)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-(TERT-BUTOXY)PROPANOATE

Chemical Property of Z-D-Ser(tbu)-ome

Chemical Property:

• PSA: 73.86000
• LogP: 2.66040
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 358

Purity/Quality:

98%Min ^*data from raw suppliers

Z-D-Ser(TBu)-OMe ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OCC(C(=O)OC)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC[C@H](C(=O)OC)NC(=O)OCC1=CC=CC=C1

Technology Process of Z-D-Ser(tbu)-ome

There total 3 articles about Z-D-Ser(tbu)-ome 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: 71.0%

O1-benzyl-O2-methyl-(2R)-aziridine-1,2-dicarboxylate (154632-86-7) + tert-butyl alcohol (75-65-0) → (2R)-2-(benzyloxycarbonylamino)-3-tert-butoxypropionic acid methyl ester (93204-37-6)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 0 - 20 ℃; for 18h;

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) + isobutene (115-11-7,15220-85-6) → (2R)-2-(benzyloxycarbonylamino)-3-tert-butoxypropionic acid methyl ester (93204-37-6)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 - 25 ℃; for 24h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2R)-2-(benzyloxycarbonylamino)-3-tert-butoxypropionic acid methyl ester (93204-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 °C

2: boron trifluoride diethyl etherate / chloroform / 18 h / 0 - 20 °C

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; chloroform;

upstream raw materials:

O₁-benzyl-O₂-methyl-(2R)-aziridine-1,2-dicarboxylate

tert-butyl alcohol

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

isobutene

Downstream raw materials:

(R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one L-tartrate

(R)-methyl 2-(2-(benzyloxycarbonylamino)ethylamino)-3-t-butoxypropanoate

(R)-3-(t-butoxymethyl)piperazine-2-one di-p-toluoyl-L-tartrate

Refernces

• 1、 -. "METHOD FOR MANUFACTURING DIPEPTIDYL PEPTIDASE-IV INHIBITOR AND INTERMEDIATE". Page/Page column 9. . Retrieved 2012/02/01.
• 2、 -. "DPP-IV INHIBITOR INCLUDING BETA-AMINO GROUP, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME FOR PREVENTING AND TREATING A DIABETES OR AN OBESITY". Page/Page column 16-17. . Retrieved 2008/12/08.