(3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS No.: 23262-84-2
• Molecular Formula: C7H12 O4
• Molecular Weight: 160.17
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID601175282
• Nikkaji Number: J818.254J
• Mol file: 23262-84-2.mol

Synonyms:23262-84-2;2,3-O-ISOPROPYLIDENE-D-ERYTHROSE;(3aS,4S,6aS)-tetrahydro-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-ol;(3aS,4S,6aS)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-ol;DTXSID601175282;(3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol;2-O,3-O-Isopropylidene-beta-L-erythrofuranose

Chemical Property of (3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol

Chemical Property:

• Boiling Point: 260.3±40.0 °C(Predicted)
• PKA: 12.19±0.40(Predicted)
• PSA: 47.92000
• Density: 1.218±0.06 g/cm3(Predicted)
• LogP: -0.14490
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 160.07355886
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

2,3-O-ISOPROPYLIDENE-D-ERYTHROSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2COC(C2O1)O)C
• Isomeric SMILES: CC1(O[C@H]2CO[C@@H]([C@H]2O1)O)C

Technology Process of (3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol

There total 8 articles about (3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 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: 94.0%

(+/-)-Isopropyliden-2,3-erythronsaeure-lacton (25494-39-7,25581-41-3,37669-02-6,53319-00-9) → (3aS,6aS)-2,2-Dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol (23262-84-2,77398-78-8,90409-96-4,108268-24-2,109715-58-4,139403-81-9,139403-82-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -70 ℃; for 0.333333h;

DOI:10.1016/0223-5234(96)88240-7

Reference yield: 77.0%

L-arabinose (5328-37-0) + 2,2-dimethoxy-propane (77-76-9) → 2,3-O-isopropylidene-β-L-erythrofuranose (23262-84-2) + α-L-2,3-O-isopropylideneerythrofuranose (108268-24-2)

Guidance literature:

L-arabinose; 2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 3h;

With sodium periodate; In water; for 12h;

With sodium carbonate; In water; pH=7; Overall yield = 77 %; Overall yield = 5.40 g;

DOI:10.1016/j.tet.2018.08.005

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → 2,3-O-isopropylidene-β-L-erythrofuranose (23262-84-2) + α-L-2,3-O-isopropylideneerythrofuranose (108268-24-2)

Guidance literature:

2,3-O-isopropylidene-D-ribofuranose; With methanol; sodium tetrahydroborate; at 4 - 20 ℃; for 4h; Inert atmosphere;

With sodium periodate; at 20 ℃; for 1h; Overall yield = 83 percent; Overall yield = 3.02 g; Inert atmosphere;

DOI:10.1021/jacs.0c01700

upstream raw materials:

2,3-O-isopropylidene-β-L-rhamnofuranose

L-arabinose

2,2-dimethoxy-propane

3,4-O-isopropylidine L-arabinopyranose

Downstream raw materials:

L-erythrose

[4R-(4α[R^*],5α)]-2,2-dimethyl-α⁴-[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]-1,3-dioxolane-4,5-dimethanol

[4S-(4α,5α(S^*))]-4-[(benzoyloxy)methyl]-5-({[(1,1-dimethylethyl)dimethylsilyl]oxy}[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]methyl)-2,2-dimethyl-1,3-dioxolane

[4S-(4α,5α(S^*))]-4-[(benzoyloxy)methyl]-2,2-dimethyl-5-{[2-(2-phenyl-1,3-dioxolan-2-yl)phenyl]hydroxymethyl}-1,3-dioxolane