(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

Base Information

Chemical Name:(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone
CAS No.:170872-96-5
Molecular Formula:C₁₆H₁₆O₇S
Molecular Weight:352.365
Hs Code.:

Synonyms:(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

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Chemical Property of (+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

Chemical Property:

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Technology Process of (+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

There total 2 articles about (+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone 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: 92.0%

: 1005-56-7
phenylcarbonochloridothioate

: 3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1
D-glucurono-3,6-lactone acetonide

: 170872-96-5
(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

Guidance literature:: With pyridine; In dichloromethane; 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h;
DOI:10.1021/jo00123a021

Reference yield:

: 14362-29-9
α-D-glucurono-γ-lactone

: 170872-96-5
(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / H₂SO₄

2: DMPA; pyridine / acetonitrile

With pyridine; sulfuric acid; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; In acetonitrile;
DOI:10.1016/j.tetlet.2005.12.113

Reference yield:

: 170872-96-5
(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

: (+)-cardiobutanolide

Guidance literature:: Multi-step reaction with 15 steps

1.1: Bu₃SnH; AIBN / toluene / 110 °C

2.1: 89 percent / aq. TFA / tetrahydrofuran

3.1: 98 percent / imidazole / dimethylformamide

4.1: 98 percent / DIBAL-H / tetrahydrofuran / -78 °C

5.1: Ag₂O / ethyl acetate

6.1: Bu₄NF / tetrahydrofuran

7.1: 88 percent / Ag₂CO₃; Celite / toluene / Heating

8.1: 92 percent / imidazole / dimethylformamide

9.1: CeCl₃ / tetrahydrofuran / -78 °C

9.2: NaBH₄; CeCl₃ / methanol / -20 °C

10.1: 95 percent / Bu₄NF / tetrahydrofuran

11.1: 90 percent / NaH; Bu₄NI / tetrahydrofuran

12.1: OsO₄; NMO / acetone; H₂O

12.2: NaIO₄ / tetrahydrofuran; H₂O

12.3: 56 percent / CeCl₃ / tetrahydrofuran / -78 °C

13.1: 91 percent / AcOH

14.1: 97 percent / Ag₂CO₃; Celite / toluene / Heating

15.1: 80 percent / H₂ / Pd/C / ethyl acetate

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); Celite; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; acetic acid; silver carbonate; trifluoroacetic acid; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 7.1: Fetizon's oxidation / 14.1: Fetizon's oxidation;
DOI:10.1016/j.tetlet.2005.12.113