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C5106

(Carbethoxymethylene)triphenylphosphorane

Name: (Carbethoxymethylene)triphenylphosphorane
Brand: ALDRICH

95%

Synonym(s):

(Ethoxycarbonylmethylene)triphenylphosphorane, Ethyl (triphenylphosphoranylidene)acetate

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About This Item

Linear Formula:

(C₆H₅)₃P=CHCO₂CH₂CH₃

CAS Number:

1099-45-2

Molecular Weight:

348.37

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

24892754

EC Number:

214-151-7

Beilstein/REAXYS Number:

754639

MDL number:

MFCD00009183

Assay:

95%

Form:

crystals

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Properties

Quality Level

200

assay

95%

form

crystals

reaction suitability

reaction type: C-C Bond Formation

mp

128-130 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C22H21O2P/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,2H2,1H3

InChI key

IIHPVYJPDKJYOU-UHFFFAOYSA-N

Description

Application

(Carbethoxymethylene)triphenylphosphorane is a Horner-Wittig reagent generally used in Horner−Wadsworth−Emmons (HWE) reaction. It is used as a reagent in the total synthesis of compounds such as (−)-oseltamivir, (+)-nakadomarin A and (−)-dictyostatin.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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High-yielding synthesis of the anti-influenza neuraminidase inhibitor (−)-oseltamivir by two ?one-pot? sequences

Ishikawa H, et al.

Chemistry?A European Journal , 16(42), 12616-12626 (2010)

Total synthesis of (−)-dictyostatin

O'Nei GW and Phillips AJ

Journal of the American Chemical Society, 128(16), 5340-5341 (2006)

The first total synthesis of nakadomarin A

Nagata T, et al.

Journal of the American Chemical Society, 125(25), 7484-7485 (2003)

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Global Trade Item Number

SKU	GTIN
C5106-100G	04061833501764
C5106-5G	04061833427675
C5106-25G	04061833501771