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Key Documents

460516

Sigma-Aldrich

Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

96%

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About This Item

Linear Formula:
ClCH2CH(OH)CH2CO2C2H5
CAS Number:
Molecular Weight:
166.60
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

optical activity

[α]23/D +14°, neat

optical purity

ee: 97% (GLC)

refractive index

n20/D 1.453 (lit.)

bp

93-95 °C/5 mmHg (lit.)

density

1.19 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C[C@@H](O)CCl

InChI

1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m1/s1

InChI key

ZAJNMXDBJKCCAT-RXMQYKEDSA-N

Application

Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate is a chiral building block that can be used:
  • To prepare allyl stannane, a precursor for the total synthesis of macrolide iriomoteolide-1b.
  • As a starting material for the synthesis of a chiral g-αmino acid fragment, which in turn is used to prepare the immunosuppressive agent FR252921.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants
Chen Y, et al.
Journal of the American Chemical Society, 141(35), 13772-13777 (2019)
Enantioselective total synthesis of the proposed structure of macrolide iriomoteolide-1b
Ye Z, et al.
Tetrahedron, 67(33), 5979-5989 (2011)

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