ChemicalBook > CAS DataBase List > 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE

2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE

Product Name
2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
CAS No.
25581-41-3
Chemical Name
2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
Synonyms
2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTOL;2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE;2,3-O-Isopropylidene-D-erythronolactone>(-)-2,3-O-Isopropylidene-D-erythronolactone;(-)-2,3-O-ISOPROPYLIDENE-D-ERYTHRONO-LACTONE;(-)-2,3-O-Isopropylidene-D-erythronolactone 98%;D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone;(?)-2,3-O-Isopropylidene-D-erythronolactone;2,3-O-Isopropylidene-D-erythronolactone;(3aR,6aR)-2,2-Dmethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
CBNumber
CB6412227
Molecular Formula
C7H10O4
Formula Weight
158.15
MOL File
25581-41-3.mol
More
Less

2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE Property

Melting point:
67-69 °C(lit.)
Boiling point:
259.7±35.0 °C(Predicted)
Density 
1?+-.0.06 g/cm3(Predicted)
refractive index 
-117 ° (C=1, H2O)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform (Slightly), Water (Slightly)
form 
Powder
color 
White to Off-white
optical activity
[α]20/D 118°, c = 1 in H2O
Water Solubility 
Soluble in water
BRN 
1282952
CAS DataBase Reference
25581-41-3(CAS DataBase Reference)
More
Less

Safety

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
2932.20.5050
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
377090
Product name
(?)-2,3-O-Isopropylidene-D-erythronolactone
Purity
98%
Packaging
1g
Price
$64.61
Updated
2025/07/31
Sigma-Aldrich
Product number
377090
Product name
(?)-2,3-O-Isopropylidene-D-erythronolactone
Purity
98%
Packaging
5g
Price
$306.6
Updated
2025/07/31
TCI Chemical
Product number
I0454
Product name
2,3-O-Isopropylidene-D-erythronolactone
Purity
>98.0%(GC)
Packaging
1g
Price
$342
Updated
2025/07/31
Usbiological
Product number
293734
Product name
2,3-O-Isopropylidene-D-erythronolactone
Packaging
5g
Price
$319
Updated
2021/12/16
TRC
Product number
I825000
Product name
2,3-O-Isopropylidene-D-erythronolactone
Packaging
1g
Price
$95
Updated
2021/12/16
More
Less

2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE Chemical Properties,Usage,Production

Uses

It undergoes Aldol condensations with silyl ketene acetals.1 Employed in spiroannulated carbohydrate synthesis.2 Convergent syntheses of a hydroxylated indolizidine,3 carbohydrate substituted benzoquinones,4 and of the oxazole segment of calyculin5 have been accomplished using this chiral synthon.

Uses

Undergoes Aldol condensations with silyl ketene acetals. Employed in spiroannulated carbohydrate synthesis. Convergent syntheses of a hydroxylated indolizidine, carbohydrate substituted benzoquinones, and of the oxazole segment of calyculin have been accomplished using this chiral synthon.

Uses

As a chiral synthon, 2,3-O-Isopropylidene-D-erythronolactone can be used for the synthesis of certain natural products such as the leukotrienes.

Synthesis

77-76-9

15667-21-7

25581-41-3

General procedure for the synthesis of 2,3-O-isopropylidene-D-erythroketonolactone from 2,2-dimethoxypropane and (3R,4R)-3,4-dihydroxydihydrofuran-2(3H)-one: Na2CO3 (42.4 g, 0.400 mol) was added batchwise to aqueous (500) solution of D-isoscorbic acid (35.2 g, 0.200 mol) at 0 °C. mL) solution. Subsequently, H2O2 (31.3% w/w, 44.0 mL, 0.450 mol) was added slowly and dropwise over 30 min. The reaction solution was stirred at 0 °C for 30 min, then warmed up to 40 °C and continued stirring for 1 h. Decolorized charcoal (Norit A, 8.0 g) was added to break down the excess peroxide and stirred until the starch-iodide test was negative (about 30 min). The reaction mixture was filtered through Celite and washed with water. The filtrate was acidified to pH 1 with 6 M HCl and subsequently concentrated under reduced pressure. To the residue was added acetone (175 mL) and MgSO4 (50 g), stirred and then 2,2-dimethoxypropane (350 mL, 2.85 mol) and TsOH-H2O (420 mg, 2.21 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 16 h. Concentrated aqueous NH4OH (20 mL) was added and stirring was continued for 10 min. The reaction mixture was diluted with Et2O (500 mL) and filtered. The filter cake was washed with Et2O (300 mL), the organic phases were combined and concentrated under reduced pressure. The residue was dissolved in Et2O, dried by adding MgSO4 (10 g), filtered through Celite and the filtrate concentrated under reduced pressure. Purification by recrystallization (Et2O/30-40 °C petroleum ether) afforded the target product 2,3-O-isopropylidene-D-erythroketonolactone (13.5 g, 43%, >99:1 dr) as a light yellow solid. [α]25D = -113 (c 1.0 in H2O); literature value [α]25D = -120 (c 1.0 in H2O); melting point 55-58 °C; literature value melting point 64-65 °C; 1H NMR (400 MHz, CDCl3) δ 1.41 (3H, s, MeCMe), 1.49 (3H, s, MeCMe), 4.39- 4.50 (2H, m, C(5)H2), 4.76 (1H, d, J=5.7 Hz, C(3)H), 4.89 (1H, dd, J=5.7,3.8 Hz, C(4)H).

References

[1] Journal of Organic Chemistry, 2000, vol. 65, # 11, p. 3432 - 3442
[2] Tetrahedron Letters, 1980, vol. 21, # 43, p. 4163 - 4166
[3] Journal of the American Chemical Society, 1983, vol. 105, # 11, p. 3661 - 3672
[4] Organic and Biomolecular Chemistry, 2005, vol. 3, # 9, p. 1795 - 1800
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 13, p. 3427 - 3437

2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE Suppliers

Americas 1 Canada 1 China 84 Europe 1 Germany 2 India 4 Japan 1 Switzerland 1 United Kingdom 6 United States 11 Global 112
TCI Chemicals (India) Pvt. Ltd.
Tel
--
Fax
--
Email
sales-in@tcichemicals.com
Country
India
ProdList
6768
Advantage
58
Alfa Aesar
Tel
--
Fax
--
Email
tech@alfa.com
Country
India
ProdList
6905
Advantage
58
Clearsynth Labs
Tel
--
Fax
--
Email
fo@clearsynth.com
Country
India
ProdList
3887
Advantage
58
More
Less

View Lastest Price from 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2,3-O-Isopropylidene-D-erythronolactone 25581-41-3
Price
US $0.00/G
Min. Order
10G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-14
Career Henan Chemical Co
Product
2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE 25581-41-3
Price
US $1.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100KG
Release date
2018-12-21

25581-41-3, 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONERelated Search:

D-ERYTHRONOLACTONE 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE 2,3-O-Isopropylidene-D-ribonic gamma-lactone 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE 2,3-CYCLOHEXYLIDENE-D-RIBONIC ACID GAMMA-LACTONE 2,3-O-ISOPROPYLIDENE-L-LYXONO-1,4-LACTONE 5-O-(TERT-BUTYLDIMETHYLSILYL)-2,3-O-ISOPROPYLIDENE-D-RIBONIC ACID GAMMA-LACTONE D-ERYTHRURONOLACTONE ACETONIDE

  • (3aR,6aR)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one
  • 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
  • Furo[3,4-d]-1,3-dioxol-4(3aH)-one, dihydro-2,2-dimethyl-, (3aR,6aR)-
  • 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTOL
  • (-)-2,3-O-ISOPROPYLIDENE-D-ERYTHRONO-LACTONE
  • (-)-2,3-O-Isopropylidene-D-erythronolactone
  • (3aR,6aR)-Dihydro-2,2-diMethyl-furo[3,4-d]-1,3-dioxol-4(3aH)-one
  • D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone
  • (-)-2,3-O-Isopropylidene-D-erythronolactone 98%
  • 2,3-<i>O</i>-Isopropylidene-<small>D</small>-erythronolactone
  • 2,3-O-Isopropylidene-D-erythronolactone&gt
  • (3aR,6aR)-2,2-Dmethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
  • (?)-2,3-<i>O</i>-Isopropylidene-<sc>D</sc>-erythronolactone
  • 25581-41-3
  • Monosaccharides
  • Specialty Synthesis
  • Carbohydrate Synthesis
  • O-Substituted Sugars
  • Sugars
  • Erythrose
  • Sugar Acids
  • Heterocycles
  • Chiral Reagents
  • Biochemistry
  • Erythrose
  • O-Substituted Sugars
  • Sugar Acids
  • Sugars
  • Carbohydrate Synthesis
  • Monosaccharides
  • Specialty Synthesis