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Merck
CN

87462

(1S,2R)-1-Methyl cis-1,2,3,6-tetrahydrophthalate

≥97.0% (sum of enantiomers, HPLC)

Synonym(s):

(1S,2R)-1-Methyl cis-4-cyclohexene-1,2-dicarboxylate, (1S,2R)-cis-4-Cyclohexene-1,2-dicarboxylic acid 1-monomethylester

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About This Item

Linear Formula:
HO2CC6H8CO2CH3
CAS Number:
88335-93-7
Molecular Weight:
184.19
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
57653249
MDL number:
MFCD00075490
Beilstein/REAXYS Number:
5262096
Assay:
≥97.0% (sum of enantiomers, HPLC)
Form:
crystals

Key Documents

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InChI

1S/C9H12O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-3,6-7H,4-5H2,1H3,(H,10,11)/t6-,7+/m1/s1

SMILES string

COC(=O)[C@H]1CC=CC[C@H]1C(O)=O

InChI key

MYYLMIDEMAPSGH-RQJHMYQMSA-N

assay

≥97.0% (sum of enantiomers, HPLC)

form

crystals

optical activity

[α]20/D +11.5±1°, c = 1% in acetone

mp

65-67 °C (lit.)

Other Notes

Chiral building block used for the synthesis of chiral cyclohexane compounds, e.g. carbapenems; Pheromones; etc.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBG8431V
1450769V
1450769
043336/1
061007/1

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S. Kobayashi et al.
Tetrahedron Letters, 25, 2557-2557 (1984)
W. Boland et al.
Helvetica Chimica Acta, 68, 2062-2062 (1985)
N. Tamura et al.
Tetrahedron Letters, 27, 3749-3749 (1986)
G.S. Hamilton et al.
The Journal of Organic Chemistry, 58, 7263-7263 (1993)
S Kobayashi et al.
Chemical & pharmaceutical bulletin, 38(2), 350-354 (1990-02-01)
A versatile chiral synthon, (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid, was obtained by an enantioselective hydrolysis of the corresponding meso diester with pig liver esterase. This enzymatic hydrolysis can easily be carried out on a multi-hundred gram scale. The chiral monoester thus obtained can

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