tert-Butyl 2-(triphenylphosphoranylidene)acetate

Base Information

• Chemical Name: tert-Butyl 2-(triphenylphosphoranylidene)acetate
• CAS No.: 35000-38-5
• Molecular Formula: C₂₄H₂₅O₂P
• Molecular Weight: 376.435
• Hs Code.: 29319090
• European Community (EC) Number: 412-880-7,609-052-4
• NSC Number: 82469
• DSSTox Substance ID: DTXSID50865742
• Nikkaji Number: J2.362.005G,J901.762C
• Wikidata: Q72504380
• Mol file: 35000-38-5.mol

Synonyms:35000-38-5;tert-Butyl 2-(triphenylphosphoranylidene)acetate;(tert-Butoxycarbonylmethylene)triphenylphosphorane;tert-Butyl(triphenylphosphoranylidene)acetate;tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate;MFCD00075545;TERT-BUTYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE;tert-butyl (triphenylphosphoranylidene) acetate;Acetic acid, (triphenylphosphoranylidene)-, 1,1-dimethylethyl ester;(t-butoxycarbonylmethylene)triphenylphosphorane;EC 412-880-7;NSC82469;NCIOpen2_009130;SCHEMBL360684;DTXSID50865742;CHEBI:188699;Acetic acid, 2-(triphenylphosphoranylidene)-, 1,1-dimethylethyl ester;BBL102550;NSC 82469;NSC-82469;STL556353;AKOS015891121;tert-butyl triphenylphosphoranediylacetate;tert-butyl triphenylphosphoranylidenacetate;carbo-t-butoxymethylene triphenylphosphorane;FT-0605352;t-butoxylcarbonylmethylenetriphenylphosphorane;t-butyloxycarbonylmethylenetriphenylphosphorane;EN300-97014;tert-butoxycarbonylmethylenetriphenylphosphorane;tert-butyl 2-triphenylphosphoranylideneacetate;(t-butoxycarbonylmethylene) triphenylphosphorane;(t-butoxycarbonylmethylene)triphenyl-phosphorane;(tertbutoxycarbonylmethylene)triphenylphosphorane;F17528;tert-butoxycarbonyl-methylenetriphenylphosphorane;tert-butoxycarbonylmethylene-triphenylphosphorane;tert-Butyl2-(triphenylphosphoranylidene)acetate;(tert-butoxy-carbonylmethylene)triphenylphosphorane;(tert-butoxycarbonyl methylene)triphenylphosphorane;(tert-butoxycarbonyl-methylene)triphenylphosphorane;(tert-Butoxycarbonylmethylene)-triphenylphosphorane;(tert-butoxycarbonylmethylene)triphenyl-phosphorane;A822500;Tert-Butoxy Carbonyl Methylene Triphenyl Phosphora;(tert-butoxycarbonylmethylene)-triphenyl phosphorane;(tert.-butoxycarbonylmethylene)-triphenylphosphorane;J-019828;tert-butyl (triphenyl-lambda5-phosphanylidene)-acetate;Triphenylphosphoranylideneacetic acid tert-butyl ester;(tert-Butoxycarbonylmethylene)triphenylphosphorane, 98%;(triphenylphosphoranylidene)-acetic acid tert-butyl ester;1-(Triphenylphosphonio)-2-oxo-2-tert-butoxyethane-1-ide;tert-butyl (triphenyl-lambda~5~-phosphanylidene)acetate;Triphenylphoranylidene acetic acid 1,1-dimethylethyl ester;1,1-Dimethylethyl (triphenyl-lambda5-phosphanylidene)acetate

Chemical Property of tert-Butyl 2-(triphenylphosphoranylidene)acetate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.89E-10mmHg at 25°C
• Melting Point: 152-155 °C(lit.)
• Refractive Index: 1.588
• Boiling Point: 503.5 °C at 760 mmHg
• Flash Point: 271.4 °C
• PSA: 36.11000
• Density: 1.13g/cm³
• LogP: 4.12440
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Sparingly soluble in water.
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 376.15921703
• Heavy Atom Count: 27
• Complexity: 475

Purity/Quality:

98% ^*data from raw suppliers

(tert-?Butoxycarbonylmethyl?ene)?triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 25-36-43-48/22-51/53
• Safety Statements: 26-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (tert-Butoxycarbonylmethylene)triphenylphosphorane is a chemical used in the synthesis of aldose reductase inhibitors, a podophyllotoxin derivative and tautomycin, a podophyllotoxin derivative and tautomycin. It Is also used in medicinal chemistry. Wittig reagent used in the synthesis of aldose reductase inhibitors, a podophyllotoxin derivative, and tautomycin.Versatile Wittig reagent used in medicinal chemistry.

Technology Process of tert-Butyl 2-(triphenylphosphoranylidene)acetate

There total 15 articles about tert-Butyl 2-(triphenylphosphoranylidene)acetate 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%

(tert-butoxycarbonylmethyl)triphenylphosphonium bromide (59159-39-6) → (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 5h;

Reference yield: 100.0%

bromoacetic acid tert-butyl ester (5292-43-3) + triphenylphosphine (603-35-0) → (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5)

Guidance literature:

bromoacetic acid tert-butyl ester; triphenylphosphine;

With sodium hydroxide;

DOI:10.1016/j.tetlet.2003.09.134

Reference yield: 98.0%

tert-Butyl chloroacetate (107-59-5) + triphenylphosphine (603-35-0) → (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5)

Guidance literature:

In benzene; for 48h; Heating;

DOI:10.1021/jo00146a025

upstream raw materials:

(tert-butyloxycarbonylmethyl)triphenylphosphonium chloride

bromoacetic acid tert-butyl ester

triphenylphosphine

t-butyl iodoacetate

Downstream raw materials:

6-[2-tert-Butoxycarbonyl-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-2,3-dimethoxy-benzoic acid ethyl ester

β,2,5-Trioxo-α-(triphenylphosphoranyliden)pyrrolidin-1-pentansaeure-1,1-dimethylethylester

Benzoic acid (2S,5R)-5-((Z)-2-tert-butoxycarbonyl-1-cyano-vinyl)-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2S,5R)-5-((E)-2-tert-butoxycarbonyl-1-cyano-vinyl)-tetrahydro-furan-2-ylmethyl ester

Refernces

A general approach to carbocyclic sugar analogs: preparation of a carbocyclic analog of β-D-fructofuranose

10.1016/0008-6215(90)80063-9

The research focuses on the development of a novel and general approach to synthesize carbocyclic sugar analogs, also known as "pseudo-sugars." The purpose of this study was to prepare a carbocyclic analog of β-D-fructofuranose 6-phosphate, which was achieved for the first time. The research concluded that the synthetic strategy was successful, offering an efficient method to transform carbohydrates into carbocyclic carbohydrates with each stereocenter already incorporated with the correct absolute configuration. The process involved a series of chemical reactions, including the use of tert-butyl-2-(triphenylphosphoranylidene)acetate, tributyltin hydride, a,a'-azobis(isobutyronitrile), lithium diisopropylamide, and diazomethane, among others.

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