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162140

Sigma-Aldrich

Diethoxymethyl acetate

96%

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About This Item

Linear Formula:
CH3COOCH(OCH2CH3)2
CAS Number:
14036-06-7
Molecular Weight:
162.18
Beilstein:
1209886
EC Number:
237-873-4
MDL number:
MFCD00009229
UNSPSC Code:
12352100
PubChem Substance ID:
24849971
NACRES:
NA.22

Assay

96%

form

liquid

refractive index

n20/D 1.399 (lit.)

density

0.993 g/mL at 25 °C (lit.)

functional group

ester

storage temp.

2-8°C

SMILES string

CCOC(OCC)OC(C)=O

InChI

1S/C7H14O4/c1-4-9-7(10-5-2)11-6(3)8/h7H,4-5H2,1-3H3

InChI key

IRUNKQSGDBYUDC-UHFFFAOYSA-N

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General description

Diethoxymethyl acetate reacts with 5-amino-6-ribitylaminouracil hydrochloride to yield 6-dioxo-(1H,3H)-9-N-ribitylpurine.

Application

Diethoxymethyl acetate was used in the synthesis of D-mannosyl, D-galactosyl and D-glucosyl theophylline nucleosides.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK2331
STBC6416V
MKBH7808V
S67651V
MKBB5847

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M Cushman et al.
Bioorganic & medicinal chemistry, 6(4), 409-415 (1998-05-23)
2,6-Dioxo-(1H,3H)-9-N-ribitylpurine (6) and 2,6-dioxo-(1H,3H)-8-aza-9-N-ribitylpurine (7) have been synthesized and evaluated as inhibitors of lumazine synthase and riboflavin synthase. Reaction of 5-amino-6-ribitylaminouracil hydrochloride (8) with diethoxymethyl acetate (9) afforded the purine 6, while diazotization of 8 afforded the 8-aza purine 7.
Rodrigo Rico-Gómez et al.
Carbohydrate research, 343(5), 855-864 (2008-02-16)
The synthesis of D-mannosyl, D-galactosyl and D-glucosyl theophylline nucleosides by diethoxymethyl acetate (DEMA)-induced cyclization of 4-amino-5-glycosylideneimino-1,3-dimethyluracil is reported. 8-Methyltheophylline derivatives of the same sugars were also prepared by Ac(2)O/H(+)-induced cyclization of their imine precursors. This approach has allowed beta-D-mannopyranosyl-, alpha-D-galactofuranosyl-

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