(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Base Information

• Chemical Name: (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
• CAS No.: 152006-17-2
• Molecular Formula: C8H12 O5
• Molecular Weight: 188.18
• DSSTox Substance ID: DTXSID30433741
• Nikkaji Number: J2.207.383D
• Wikidata: Q72485958
• Mol file: 152006-17-2.mol

Synonyms:152006-17-2;2,3-O-isopropylidene-L-lyxono-1,4-lactone;(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one;2,3-O-Isopropylidene-L-lyxonic acid-1,4-lactone;(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one;2,3-O-Isopropylidene-D-lyxono-1,4-lactone;SCHEMBL2158911;DTXSID30433741;56543-10-3;MFCD03425584;AKOS006278360;AS-82166;CS-0016277;F12788;A884045;2-O,3-O-Isopropylidene-L-lyxonic acid 1,4-lactone;W-201355;(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one

Chemical Property of (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property:

• Melting Point: 95-97°C
• PSA: 64.99000
• LogP: -0.57580
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetone (Sparingly), Chloroform (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

98% ^*data from raw suppliers

2,3-O-Isopropylidene-L-lyxonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(=O)C2O1)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H](OC(=O)[C@@H]2O1)CO)C
• Uses: Intermediate in the synthesis of the α-L-fucosidase inhibitor, Deoxyfuconojirimycin.

Technology Process of (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

There total 10 articles about (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 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: 84.0%

(3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone (89747-54-6) → 2,3-O-isopropylidene-L-lyxono-1,4-lactone (152006-17-2)

Guidance literature:

With potassium hydroxide; for 3h; Ambient temperature;

DOI:10.1016/S0968-0896(96)00167-8

Reference yield: 84.0%

2,3-Isopropylidene-D-gulono-γ-lactone (23843-32-5) → 2,3-O-isopropylidene-L-lyxono-1,4-lactone (152006-17-2)

Guidance literature:

2,3-Isopropylidene-D-gulono-γ-lactone; With periodic acid; In tetrahydrofuran; for 0.333333h;

With sodium cyanoborohydride; In acetic acid; for 1.5h;

DOI:10.1016/j.carres.2005.10.002

Reference yield: 64.8%

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 2,3-O-isopropylidene-L-lyxono-1,4-lactone (152006-17-2)

Guidance literature:

2,3-O-isopropylidene-D-ribonic-γ-lactone; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

With water; potassium hydroxide; In 1,4-dioxane; for 3h;

upstream raw materials:

3,4-O-Isopropylidene-L-arabinuronic acid 2,5-lactone

4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester

(3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone

2,3-Isopropylidene-D-gulono-γ-lactone

Downstream raw materials:

5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone

2,3-O-isopropylidene-L-lyxofuranose

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Refernces

• 1、 Batra, Hitesh,Moriarty, Robert M.,Penmasta, Raju,Sharma, Vijay,Stanciuc, Gabriela,Staszewski, James P.,Tuladhar, Sudersan M.,Walsh, David A.,Datla, Satyanarayana,Krishnaswamy, Sunderraj. "A concise, efficient and production-scale synthesis of a protected L-lyxonolactone derivative: An important aldonolactone core". . p. 484 - 486. Retrieved 2006.
• 2、 Choi, Hongseok,Jacobson, Kenneth A.,Yu, Jinha,Jeong, Lak Shin. "Design and synthesis of 2,6-disubstituted-4′-selenoadenosine- 5′-N,N-dimethyluronamide derivatives as human A3 adenosine receptor antagonists". . . Retrieved 2021/05/03.
• 3、 -. "Antioxidant composition comprising marliolide derivatives". Paragraph 0039-0041; 0054-0057. . Retrieved 2019/11/23.