254606
(S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯
96%
别名:
α,β-异亚丙基-L-甘油酸甲酯, 2,3-O-异亚丙基-L-甘油酸甲酯, 甲基α,β-异亚丙基-L-甘油酸酯
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关于此项目
经验公式（希尔记法）:
C7H12O4
化学文摘社编号:
分子量:
160.17
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4292352
产品名称
(S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯, 96%
form
liquid
InChI
1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1
SMILES string
COC(=O)[C@@H]1COC(C)(C)O1
InChI key
DOWWCCDWPKGNGX-YFKPBYRVSA-N
assay
96%
optical activity
[α]20/D −8.5°, c = 1.5 in acetone
optical purity
ee: ≥96.0% (GLC)
refractive index
n20/D 1.425 (lit.)
bp
84-86 °C/15 mmHg (lit.)
density
1.106 g/mL at 25 °C (lit.)
functional group
ester
ether
ketal
Quality Level
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Application
(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate can be used:
- As a chiral building block to make the key tetrahydrofuran subunit of (−)-gymnodimine, a marine algal toxin.
- To prepare an enedione by reacting with dimethyl methylphosphonate, BuLi, and phenylglyoxal, which in turn is used to synthesize cyclopentenone derivatives.
- As a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria.
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
172.4 °F - closed cup
flash_point_c
78 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Annulation of 2-Oxoalkylidenetriphenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones
Kitano H, et al.
Synthesis, 2002(06), 0739-0744 (2002)
Sigrid C J De Keersmaecker et al.
The Journal of biological chemistry, 280(20), 19563-19568 (2005-03-26)
We describe an original, short, and convenient chemical synthesis of enantiopure (S)-4,5-dihydroxy-2,3-pentanedione (DPD), starting from commercial methyl (S)-(-)-2,2-dimethyl-1,3-dioxolane-4-carboxylate. DPD is the precursor of autoinducer (AI)-2, the proposed signal for bacterial interspecies communication. AI-2 is synthesized by many bacterial species in
James D White et al.
The Journal of organic chemistry, 72(5), 1717-1728 (2007-02-01)
Two principal subunits of the marine algal toxin (-)-gymnodimine were synthesized. A trisubstituted tetrahydrofuran representing C10-C18 of the toxin was prepared via a highly stereoselective iodine-mediated cyclization of an acyclic alkene bearing a bis-2,6-dichlorobenzyl (DCB) ether. The formation of a
Studies on the Synthesis of (−)-Gymnodimine. Subunit Synthesis and Coupling
White JD, et al.
The Journal of Organic Chemistry, 72(5), 1717-1728 (2007)
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