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文件

254606

(S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯

Name: (<I>S</I>)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯
Brand: ALDRICH

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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About This Item

经验公式（希尔记法）:

C₇H₁₂O₄

CAS号:

60456-21-5

分子量:

160.17

Beilstein:

4292352

MDL编号:

MFCD00066526

UNSPSC代码:

12352005

PubChem化学物质编号:

24855396

NACRES:

NA.22

质量水平

200

检测方案

96%

形式

liquid

旋光性

[α]20/D −8.5°, c = 1.5 in acetone

光学纯度

ee: ≥96.0% (GLC)

折射率

n20/D 1.425 (lit.)

bp

84-86 °C/15 mmHg (lit.)

密度

1.106 g/mL at 25 °C (lit.)

SMILES字符串

COC(=O)[C@@H]1COC(C)(C)O1

InChI

1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1

InChI key

DOWWCCDWPKGNGX-YFKPBYRVSA-N

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应用

(−)-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.

WGK

WGK 3

闪点(°F)

closed cup

闪点(°C)

closed cup

个人防护装备

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Annulation of 2-Oxoalkylidenetriphenylphosphoranes with enediones: A one-step synthesis of substituted cyclopentenones

Kitano H, et al.

Synthesis, 2002(06), 0739-0744 (2002)

Studies on the Synthesis of (−)-Gymnodimine. Subunit Synthesis and Coupling

White JD, et al.

The Journal of Organic Chemistry, 72(5), 1717-1728 (2007)

Chemical synthesis of (S)-4,5-dihydroxy-2,3-pentanedione, a bacterial signal molecule precursor, and validation of its activity in Salmonella typhimurium.

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

Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling.

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

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