(+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER

Base Information

• Chemical Name: (+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER
• CAS No.: 89524-98-1
• Molecular Formula: C₁₀H₂₀NO₇P
• Molecular Weight: 297.245
• Hs Code.: 29319090
• Mol file: 89524-98-1.mol

Synonyms:Aceticacid, (dimethoxyphosphinyl)[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester(9CI);Methyl 2-[(tert-butoxycarbonyl)amino]-2-(dimethoxyphosphoryl)acetate;

Chemical Property of (+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER

Chemical Property:

• Vapor Pressure: 1.46E-06mmHg at 25°C
• Melting Point: 67-71°C
• Refractive Index: 1.446
• Boiling Point: 398.6 °C at 760 mmHg
• PKA: 9.63±0.46(Predicted)
• Flash Point: 194.9 °C
• PSA: 109.97000
• Density: 1.204 g/cm³
• LogP: 1.88700
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

(±)-Boc-α-phosphonoglycine trimethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Wittig-Horner reagent for preparing (Z)-Boc-protected dehydroamino acid derivatives. It is used as Wittig-Horner reagent for preparing (Z)-Boc-protected dehydroamino acid derivatives and saturated, unnatural amino acids by subsequent asymmetric hydrogenation.

Technology Process of (+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER

There total 7 articles about (+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; under 750.075 Torr;

DOI:10.1016/j.tet.2007.09.078

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl 2-amino-2-(dimethoxyphosphoryl)acetate (89537-21-3) → trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1)

Guidance literature:

DOI:10.1021/jo0106593

Reference yield: 93.0%

tert-butyl carbazate (4248-19-5) + methyl 2-diazo-2-(dimethoxyphosphoryl)acetate (60190-78-5) → trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1)

Guidance literature:

With dirhodium tetraacetate;

DOI:10.1016/S0040-4039(00)01120-5

upstream raw materials:

di-tert-butyl dicarbonate

methyl 2-amino-2-(dimethoxyphosphoryl)acetate

tert-butyl carbazate

methyl 2-diazo-2-(dimethoxyphosphoryl)acetate

Downstream raw materials:

methyl (R,Z)-4-benzyloxy-2-tert-butoxycarbonylamino-5-hydroxy-2-pentenoate

(R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(E)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

Refernces

• 1、 -. "SYNTHESIS OF (S)-6-HYDROXYTRYPTOPHAN AND DERIVATIVES THEREOF". Page/Page column 14-15. . Retrieved 2020/07/07.
• 2、 Azuma, Hiroki,Okano, Kentaro,Fukuyama, Tohru,Tokuyama, Hidetoshi. "Preparation of horner-wadsworth-emmons reagent: Methyl 2- benzyloxycarbonylamino-2-(dimethoxy-phosphinyl)acetate". . p. 152 - 161. Retrieved 2014/04/03.