ChemicalBook > CAS DataBase List > (-)-2,3-O-Isopropylidene-D-threitol

(-)-2,3-O-Isopropylidene-D-threitol

Product Name
(-)-2,3-O-Isopropylidene-D-threitol
CAS No.
73346-74-4
Chemical Name
(-)-2,3-O-Isopropylidene-D-threitol
Synonyms
(4R,5R)-;2,3-O-isopropylidene threitol;2,3-O-ISOPROPYLIDENE-D-THREITOL;2,2-O-Isopropylidene-D-Threitol;2-O,3-O-Isopropylidene-D-threitol;2,3-DI-O-ISOPROPYLIDENE-D-THREITOL;(+)-2,3-O-ISOPROPYLIDINE-D-THREITOL;2,2-O-ISOPROPYLIDENE-D-THREITOL,99%;(-)-2,3-O-Isopropylidene-D-threitol;(-)-2,3-O-Isopropylidine-D-Threitol
CBNumber
CB8428640
Molecular Formula
C7H14O4
Formula Weight
162.18
MOL File
73346-74-4.mol
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(-)-2,3-O-Isopropylidene-D-threitol Property

Melting point:
48-51 °C(lit.)
Boiling point:
91-93 °C0.01 mm Hg(lit.)
alpha 
-3.1 º (c=5, CHCl3 26 ºC)
Density 
1.0585 (rough estimate)
refractive index 
-4 ° (C=5, Acetone)
Flash point:
>230 °F
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Chloroform, Dichloromethane, Ethyl Acetate, THF
pka
13.90±0.10(Predicted)
form 
Oil
color 
Yellow
Water Solubility 
Soluble in water.
Sensitive 
Hygroscopic
BRN 
1798
CAS DataBase Reference
73346-74-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
F 
3-10
HS Code 
29329970
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
I0375
Product name
(-)-2,3-O-Isopropylidene-D-threitol
Purity
>98.0%(GC)
Packaging
1g
Price
$80
Updated
2025/07/31
TCI Chemical
Product number
I0375
Product name
(-)-2,3-O-Isopropylidene-D-threitol
Purity
>98.0%(GC)
Packaging
5g
Price
$328
Updated
2025/07/31
TRC
Product number
I868935
Product name
2,3-O-Isopropylidene-D-threitol
Packaging
1g
Price
$55
Updated
2021/12/16
Usbiological
Product number
I9041-01
Product name
2,3-Di-O-isopropylidene-D-threitol
Packaging
500mg
Price
$333
Updated
2021/12/16
Chem-Impex
Product number
32381
Product name
(-)-2,3-O-Isopropylidene-D-threitol,98%(GC)
Purity
98%(GC)
Packaging
1G
Price
$33.6
Updated
2021/12/16
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(-)-2,3-O-Isopropylidene-D-threitol Chemical Properties,Usage,Production

Chemical Properties

Colorless to light yellow liqui

Uses

(-)-2,3-O-Isopropylidene-D-threitol is used in the synthesis of the optically active enantiomorphic 2,3-butanediols. It react with toluene-4-sulfonyl chloride to get O2,O3-isopropylidene-O1,O4-bis-(toluene-4-sulfonyl)-D-threitol.

Synthesis

37031-29-1

73346-74-4

General procedure for the synthesis of 2,3-O-isopropylidene-D-sitosterol from dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate: an anhydrous tetrahydrofuran (120 ml) solution of lithium aluminium hydride (10 g, 267 mmol) was stirred and refluxed under nitrogen protection for 30 min. Subsequently, a solution of anhydrous tetrahydrofuran (200 ml) of 2,3-O-isopropylidene-L-tartaric acid dimethyl ester (53 g, 243 mmol) was slowly added dropwise with stirring, and heat generated during the reaction induced a mild reflux. After continuing the reflux reaction for 3 h, the reaction solution was cooled to 0 °C. Water (8.4 ml), 4M sodium hydroxide solution (8.4 ml) and water (32 ml) were added sequentially to the reaction solution. The resulting precipitate was removed by filtration and the filtrate was extracted with ether (using Soxhlet extractor). The organic phases were combined, dried and concentrated under reduced pressure to give 2,3-O-isopropylidene-L-sitosterol (35 g, 216 mmol, 89% yield). The product was identified by 1H NMR (CDCl3): δ 3.98 (m, 2H), 3.77 (m, 4H), 3.64 (s, 2H), 1.45 (s, 6H); 13C NMR (CDCl3) showed the characteristic peaks: δ 109.53, 78.24, 62.25, 27.28; low resolution electron bombardment mass spectrometry (LREIMS) revealed that molecular ion peak m/z 162.1 (M+). The crude product obtained can be directly used in the subsequent reaction.

References

[1] Chirality, 2018, vol. 30, # 4, p. 342 - 350
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3762 - 3765
[3] European Journal of Organic Chemistry, 2011, # 23, p. 4465 - 4471
[4] Heterocycles, 2012, vol. 86, # 1, p. 687 - 695
[5] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 10698 - 10706

(-)-2,3-O-Isopropylidene-D-threitol Preparation Products And Raw materials

Raw materials

Preparation Products

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(-)-2,3-O-Isopropylidene-D-threitol Suppliers

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View Lastest Price from (-)-2,3-O-Isopropylidene-D-threitol manufacturers

Career Henan Chemical Co
Product
(-)-2,3-O-Isopropylidene-D-threitol 73346-74-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
Customized
Release date
2019-07-02

73346-74-4, (-)-2,3-O-Isopropylidene-D-threitolRelated Search:

Dimethyl sulfoxide Dimethyl fumarate Lithium diisopropylamide 1,4-Dioxane N,N-Diisopropylethylamine Isomalt N,N-Dimethylformamide 6-O-ALPHA-D-GLUCOPYRANOSYL-D-GLUCITOL Chloromethyl isopropyl carbonate 2,2-Dimethyl-1,3-dioxolane-4-methanol Selenium dioxide ISOMALTOSE Dimethyl carbonate DIOXOPROMETHAZINE HCL ETHANE Dimethyl phthalate Dimethyl sebacate Dimethyl ether

  • D(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIMETHANOL
  • 2,3-DI-O-ISOPROPYLIDENE-D-THREITOL
  • (+)-2,3-O-ISOPROPYLIDINE-D-THREITOL
  • 2,3-O-ISOPROPYLIDENE-D-THREITOL
  • (4S,5R)-(-)-4,5-BIS(HYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
  • (4R-TRANS) 1,3-DIOXOLANE-4,5-DIMETHANOL-2,2-DIMETHYL BUTANOIC ACID
  • (4R-TRANS)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIMETHANOL
  • (4R,5R)-4,5-Dihydroxymethyl-2,2-dimethyl dioxolane
  • (4R,5R)-(-)-4,5-BIS(HYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
  • (4R,5R)-4,5-BIS(HYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
  • (4R,5R)-(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIMETHANOL
  • (4R,5R)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIMETHANOL
  • (-)-2,3-<i>O</i>-Isopropylidene-<small>D</small>-threitol
  • (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol,99%e.e.
  • 2,3-O-isopropylidene threitol
  • (4R,5R)-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol, (4R,5R)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
  • (-)-2,3-O-Isopropylidene-D-threitol, (4R,5R)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
  • [(4R,5R)-5-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
  • 1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-, (4R-trans)-
  • (-)-2-O,3-O-Isopropylidene-D-threitol
  • (4R)-2,2-Dimethyl-1,3-dioxolane-4α,5β-dimethanol
  • 2-O,3-O-Isopropylidene-D-threitol
  • ((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)dimethanol
  • (4R,5R)-trans-4,5-di(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane
  • (-)-2,3-O-Isopropylidene-D-threitol,99%
  • (-)-2-3-O-Isopropylidene-D-threitol ,98%
  • (4R,5R)-
  • (4R,5R)-(-)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (4R,5R)-(-)-2,2-Dimethyl-1,3-dioxolane-4,5-dimethanol
  • 2,2-O-ISOPROPYLIDENE-D-THREITOL,99%
  • 1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-, (4R,5R)-
  • (-)-2,3-O-Isopropylidene-D-threitol&gt
  • (-)-2,3-O-Isopropylidene-D-threitol USP/EP/BP
  • (-)-2,3-O-Isopropylidene-D-threitol
  • (-)-2,3-iOi-Isopropylidene-smallDsmall-threitol
  • (-)-2,3-O-Isopropylidine-D-Threitol
  • 2,2-O-Isopropylidene-D-Threitol
  • (-)-2,3-Di-O-isopropylidene-D-threitol
  • 73346-74-4
  • 73346-74-7
  • Carbohydrate Synthesis
  • Asymmetric Synthesis
  • Alcohols
  • Glycidyl Compounds, etc. (Chiral)
  • Sugar Alcohols
  • Dioxolanes
  • O-Substituted Sugars
  • Chiral Building Blocks
  • Sugars
  • Dioxanes & Dioxolanes
  • Organic Building Blocks
  • Monosaccharides
  • Specialty Synthesis
  • Heterocycles series
  • chiral
  • Chiral Reagents
  • Biochemistry
  • Chiral Building Blocks
  • Dioxanes & Dioxolanes