(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:20720-51-8
Molecular Formula:C₉H₁₄O₄
Molecular Weight:186.208
Hs Code.:
Nikkaji Number:J1.696.775K
Mol file:20720-51-8.mol

Synonyms:20720-51-8;(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole;(3aR,5S,6aR)-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;(2S)-2-[(3aR,5S,6aR)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]oxirane;SCHEMBL20360759;CS-0054298;1-O,2-O-Isopropylidene-5,6-anhydro-3-deoxy-beta-L-lyxo-hexofuranose

Suppliers and Price of (3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
5,6-Anhydro-3-deoxy-1,2-O-(1-methylethylidene)-β-L-lyxo-hexofuranose
50mg
$ 85.00

Crysdot
(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 95+%
5g
$ 865.00

Chemenu
(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 95%
5g
$ 816.00

Alichem
(3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole
5g
$ 890.46

Total 6 raw suppliers

Chemical Property of (3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Boiling Point:110-111 °C(Press: 10 Torr)
Density:1?+-.0.06 g/cm3(Predicted)
Solubility.:Dichloromethane; Ether
XLogP3:0.4
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:186.08920892
Heavy Atom Count:13
Complexity:228

Purity/Quality:

99% ^*data from raw suppliers

5,6-Anhydro-3-deoxy-1,2-O-(1-methylethylidene)-β-L-lyxo-hexofuranose ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1(OC2CC(OC2O1)C3CO3)C
Isomeric SMILES:CC1(O[C@@H]2C[C@H](O[C@@H]2O1)[C@@H]3CO3)C
Uses 5,6-Anhydro-3-deoxy-1,2-O-(1-methylethylidene)-β-L-lyxo-hexofuranose is an intermediate in synthesizing 6R,7S,8aR-Glucosepane Tri-TFA Salt (G595310), one of the eight diastereomers of glucosepane. Glucosepane is a structurally complex protein posttranslational modification that is believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging.

Technology Process of (3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

There total 2 articles about (3aR,5S,6aR)-2,2-Dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 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: 74.0%

: 457073-50-6
6-O-benzoyl-3-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-xylo-hexofuranose

: 2457-93-4,20720-51-8,75646-87-6
(3aR,5R,6aR)-2,2-dimethyl-5-((S)-oxiran-2-yl)tetrahydrofuro[3,2-d][1,3]dioxole

: 3-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-xylo-hexofuranose

Guidance literature:: With sodium methylate; In methanol; chloroform; at 20 ℃; for 12h;
DOI:10.1135/cccc20020622

Reference yield: 12.0%

: 20720-47-2
6-O-benzoyl-3-deoxy-1,2-O-isopropylidene-5-O-tosyl-α-D-ribo-hexofuranose

: 3-deoxy-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-ribo-hexofuranose

: 20720-51-8
(3aR,5S,6aR)-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With sodium methylate; In methanol; chloroform; at 20 ℃; for 12h;
DOI:10.1135/cccc20020622

Reference yield:

: 20720-51-8
(3aR,5S,6aR)-2,2-dimethyl-5-[(2S)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

: C₃₄H₅₄O₆Si

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi; HMPA / 1 h / 5 °C

1.2: 12 h / 23 °C

2.1: MeOH / diethyl ether / 1 h / 23 °C

3.1: 93 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 23 °C

4.1: BF₃*Et₂O / CH₂Cl₂ / 18 h / 23 °C

5.1: ImH / dimethylformamide / 12 h / 50 °C

6.1: OsO₄; NMO / 2-methyl-propan-2-ol / 12 h / 23 °C

7.1: NaIO₄/SiO₂ / CH₂Cl₂ / 1.5 h / 23 °C

8.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / -90 - 23 °C

9.1: NaBH₄; (H₂NCH₂)2; H₂ / Ni(OAc)2 / ethanol / 5 h / 23 °C / 760.05 Torr

With 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; silica gel; ethylenediamine; triethylamine; nickel diacetate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 8.1: Wittig olefination;
DOI:10.1016/j.bmcl.2007.01.096