2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE

Base Information

• Chemical Name: 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE
• CAS No.: 25581-41-3
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 2932999099
• Mol file: 25581-41-3.mol

Synonyms:Erythronicacid, 2,3-O-isopropylidene-, g-lactone, D- (8CI);Furo[3,4-d]-1,3-dioxol-4(3aH)-one,dihydro-2,2-dimethyl-, (3aR-cis)-;(3AR,6aR)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one;

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

Chemical Property:

• Vapor Pressure: 0.0128mmHg at 25°C
• Melting Point: 67-69 °C(lit.)
• Refractive Index: -117 ° (C=1, H2O)
• Boiling Point: 259.7 °C at 760 mmHg
• Flash Point: 112.4 °C
• PSA: 44.76000
• Density: 1.207 g/cm³
• LogP: 0.06330
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Water (Slightly)
• Water Solubility.: Soluble in water

Purity/Quality:

98%, ^*data from raw suppliers

2,3-O-Isopropylidene-D-erythronolactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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. 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. 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.

Technology Process of 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE

There total 4 articles about 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,2-dimethoxy-propane (77-76-9) + D-erythronolactone (15667-21-7) → D-erythronolactone acetonide (25581-41-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 4h; Heating;

DOI:10.1021/jo991722f

Reference yield: 76.0%

2,2-dimethoxy-propane (77-76-9) + D-erythronolactone (15667-21-7) → D-erythronolactone acetonide (25581-41-3) + (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester (189996-59-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone;

DOI:10.1039/a607158i

Reference yield: 48.4%

2,2-dimethoxy-propane (77-76-9) + D-erythronolactone (15667-21-7) → D-erythronolactone acetonide (25581-41-3) + C12H22O6

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.15227/orgsyn.063.0127

upstream raw materials:

2,2-dimethoxy-propane

D-erythronolactone

acetone

Downstream raw materials:

(4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide

(3aR,6aR)-2,2-Dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

2,5-anhydro-1-deoxy-3,4-O-isopropylidene-D-erythro-pent-1-enitol

(4R,5S)-4-(4-Methoxy-benzyloxymethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane