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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
Pricing and availability is not currently available.

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4148
STBL3843
STBL1678
STBK6203
STBJ3308

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4-Chloromethyl-2,2-dimethyl-1,3-dioxolane 97%

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)
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)
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)
2- and 8- functionalized 1,4,7,10-tetraoxaspiro[5.5]undecanes.: II. Synthesis of (+)-E,E and (?)-Z,E structures from chiral isopropylideneglycerols.
Marielle Lemaire
Tetrahedron Asymmetry, 4. 9, 2101-2108 (1993)
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