1,4-Anhydro-2,3-O-isopropylidene-4-thio-D-ribitol

Base Information

• Chemical Name: 1,4-Anhydro-2,3-O-isopropylidene-4-thio-D-ribitol
• CAS No.: 596103-06-9
• Molecular Formula: C8H14O3S
• Molecular Weight: 190.263
• Mol file: 596103-06-9.mol

Synonyms:((3aS,4R,6aR)-2,2-Dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-methanol;(3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl-methanol;1,4-anhydro-2,3-O-isopropylidene-4-thio-D-ribitol;1,4-anhydro-4-thio-D-ribitol;

Chemical Property of 1,4-Anhydro-2,3-O-isopropylidene-4-thio-D-ribitol

Chemical Property:

• Melting Point: 56-60 °C
• Boiling Point: 301.2±32.0 °C(Predicted)
• PKA: 14.14±0.10(Predicted)
• PSA: 63.99000
• Density: 1.178±0.06 g/cm3(Predicted)
• LogP: 0.61420

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-Anhydro-2,3-O-isopropylidene-4-thio-D-ribitol

There total 22 articles about 1,4-Anhydro-2,3-O-isopropylidene-4-thio-D-ribitol 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: 98.0%

(3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4- d][1,3]dioxole-4-carbaldehyde (666750-24-9) → ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol (596103-06-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/jm034098e DOI:10.1021/jm050595e

Reference yield: 81.0%

tert-butyl (((3aS.4R.6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane (1320269-77-9) → ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol (596103-06-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 8h;

DOI:10.1021/ml2001054

Reference yield: 76.0%

lead(IV) tetraacetate (546-67-8) + D-gulono-γ-lactone (96243-58-2) → ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol (596103-06-9)

Guidance literature:

lead(IV) tetraacetate; D-gulono-γ-lactone; In ethyl acetate; at 0 ℃; for 0.25h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h; Further stages.;

DOI:10.3987/COM-07-11250

upstream raw materials:

(3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4- d][1,3]dioxole-4-carbaldehyde

(3aR,6S,7R,7aR)-6-Methoxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-7-ol

2,3:5,6-di-O-isopropylidene-D-gulitol

methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

Downstream raw materials:

benzoic acid (3aS,4R,6aR)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

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