CID 11021409

Base Information

• Chemical Name: CID 11021409
• CAS No.: 90473-01-1
• Molecular Formula: C14H23NO3
• Molecular Weight: 253.33732
• DSSTox Substance ID: DTXSID00452247
• Nikkaji Number: J594.191A
• Mol file: 90473-01-1.mol

Synonyms:90473-01-1;Ethyl 2-[[(1R,2R,5R)-2-hydroxy-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanylidene]amino]acetate;ZINC22059003;DTXSID00452247;XVHYGWSRXODAMH-GPCCPHFNSA-N;N-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]-glycine Ethyl Ester;N-[(1beta,5beta)-2,6,6-Trimethyl-2beta-hydroxybicyclo[3.1.1]heptane-3-ylidene]glycine ethyl ester

Chemical Property of CID 11021409

Chemical Property:

• Boiling Point: 329.7±27.0 °C(Predicted)
• PKA: 13.41±0.40(Predicted)
• PSA: 58.89000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 1.80750
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Dichloromethane, Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 253.16779360
• Heavy Atom Count: 18
• Complexity: 389

Purity/Quality:

99% ^*data from raw suppliers

(+)-(1R,2R,5R)--Ethyl[(2-Hydroxypinan-3-ylene)amino]acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN=C1CC2CC(C2(C)C)C1(C)O
• Isomeric SMILES: CCOC(=O)CN=C1C[C@H]2C[C@@H]([C@@]1(C)O)C2(C)C
• Uses: (+)-(1R,2R,5R)-2-Hydroxy-3-pinanone (H952000) derivative. Intermediate in the synthesis of D-erythro-Sphingosine (S681000).

Technology Process of CID 11021409

There total 4 articles about CID 11021409 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: 95.0%

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1) + GlyOEt*HCl (459-73-4) → (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate (90473-01-1)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1016/S0040-4039(98)00172-5

Reference yield:

glycine ethyl ester hydrochloride (623-33-6) + (-)-(2R,3R,5R)-2-hydroxy-3-pinanone (1845-25-6,10136-65-9,20536-50-9,73466-08-7,84236-04-4,125073-44-1,24047-72-1) → (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate (90473-01-1)

Guidance literature:

glycine ethyl ester hydrochloride; With ammonia; In toluene; for 1h;

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone; With boron trifluoride diethyl etherate; for 5h; Dean-Stark; Reflux;

Reference yield:

(-)-α-pinene (7785-26-4,25766-18-1) → (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate (90473-01-1)

Guidance literature:

DOI:10.1016/S0040-4039(01)91546-1

upstream raw materials:

(-)-(2R,3R,5R)-2-hydroxy-3-pinanone

GlyOEt*HCl

(-)-α-pinene

glycine ethyl ester hydrochloride

Downstream raw materials:

C₂₁H₃₅NO₅

C₂₁H₃₅NO₅

L-phosphinothricin

(S)-(+)-phosphinothricin

Refernces

• 1、 -. "ALPHA-GALACTOSYLCERAMIDE ANALOGS, THEIR METHODS OF MANUFACTURE, INTERMEDIATE COMPOUNDS USEFUL IN THESE METHODS, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM". Page/Page column 42-43. . Retrieved 2008/12/05.
• 2、 Minowa, Nobuto,Hirayama, Masao,Fukatsu, Shunzo. "ASYMMETRIC SYNTHESIS OF (+)-PHOSPHINOTHRICIN and (+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID". . p. 1147 - 1150. Retrieved 2007/10/02.