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241806

Sigma-Aldrich

(R)-(−)-2,2-Dimethyl-1,3-dioxolane-4-methanol

98%

Synonym(s):

2,3-Isopropylidene-sn-glycerol, L-α,β-Isopropylideneglycerol, L-2,3-O-isopropylidene-sn-glycerol

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$75.90

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1 G
$36.20
5 G
$75.90

About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
14347-78-5
Molecular Weight:
132.16
Beilstein/REAXYS Number:
80117
MDL number:
MFCD00003213
UNSPSC Code:
12352005
PubChem Substance ID:
24854331
NACRES:
NA.22
form:
liquid
assay:
98%

$36.20

In StockDetails

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Quality Level

100

assay

98%

form

liquid

optical activity

[α]20/D −13.7°, neat

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.434 (lit.)

bp

72-73 °C/8 mmHg (lit.)

density

1.062 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl
ketal

storage temp.

2-8°C

SMILES string

CC1(C)OC[C@@H](CO)O1

InChI

1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m1/s1

InChI key

RNVYQYLELCKWAN-RXMQYKEDSA-N

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Application

(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol may be used to prepare:
  • (R)-2,2-Dimethyl-4-benzoxymethyl-1,3-dioxolane.[1]
  • ((S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate)-1,3-dioxolane.[2]
  • (S)-Glyceraldehyde acetonide.[3]
  • Tetraoxaspiroundecanes[4], diglycerides,[5] glyceryl phosphates,[6] and spiropyrans.[7]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4148
STBL3843
STBL1678
STBK6203
STBJ3308

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Sigma-Aldrich

550604

4-Chloromethyl-2,2-dimethyl-1,3-dioxolane

A cytosine analogue containing a conformationally flexible acyclic linker for triplex formation at sites with contiguous GC base pairs.
Xiang G and McLaughlin LW.
Tetrahedron, 54(3), 375-392 (1998)
René Pemha et al.
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A series of novel substituted 1-O-alkylglycerols (AKGs) containing methoxy (8), gem-difluoro (9), azide (10) and hydroxy (11) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid (12). The structures of these new synthesized AKGs
Synthesis of a `reverse ester? analogue of 1,2-sn-diglycerides from (S)-1,2-di-O-isoprophylideneglycerol; efficient, stereospecific nucleophilic displacement via a triflate at glycerol C-2
Bernard T Golding, et al.
Tetrahedron Letters, 34, 6459-6462 (1993)
Enantioselective synthesis of N1999A2.
Ji N, et al.
Journal of the American Chemical Society, 128(46), 14825-14825 (2006)
S-Aryl-L-cysteine S,S-dioxides: design, synthesis, and evaluation of a new class of inhibitors of kynureninase
Rajesh K. Dua,
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