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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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About This Item

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

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.)

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.
  • ((S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate)-1,3-dioxolane.
  • (S)-Glyceraldehyde acetonide.
  • Tetraoxaspiroundecanes, diglycerides, glyceryl phosphates, and spiropyrans.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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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)
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.
Marine drugs, 18(2) (2020-02-23)
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
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,
Journal of the American Chemical Society, 115, 4, 1264-1270 (1993)
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