Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

Base Information

Chemical Name:Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester
CAS No.:457645-24-8
Molecular Formula:C₂₂H₃₀O₆S₂
Molecular Weight:454.609
Hs Code.:

Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

Synonyms:Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

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Chemical Property of Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

There total 6 articles about Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester 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: 70.0%

: 75-15-0,12122-00-8
carbon disulfide

: 457645-23-7
(3aR,4R,5aR,9aR,9bS)-4-(benzyloxy)-2,2,8,8-tetramethylhexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-5-ol

: 74-88-4
methyl iodide

: 457645-24-8
Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

Guidance literature:: With sodium hydride;
DOI:10.1055/s-2002-31900

Reference yield:

: 457645-20-4
1-phenyl-1,2-dideoxy-7-O-(phenoxythiocrbonyl)-4,5:6,8-di-O-isopropylidene-D-talo-D-glycero-oct-1-yne

: 457645-24-8
Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Bu₃SnH; AIBN / toluene / 12 h / 85 °C

2: 73 percent / NaH

3: O₃; Me₂S

4: NaBH₄; CeCl₃

5: 70 percent / NaH

With sodium tetrahydroborate; cerium(III) chloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; ozone; In toluene;
DOI:10.1055/s-2002-31900

Reference yield:

: 631918-09-7
(3aR,4R,5Z,5aS,9aR,9bS)-5-benzylidene-2,2,8,8-tetramethyl hexahydro-3aH-[1,3]dioxolo[4,5-h][1,3]benzodioxin-4-ol

: 457645-24-8
Dithiocarbonic acid O-((3aR,4R,5aS,9aR,9bS)-4-benzyloxy-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-5-yl) ester S-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 80 percent / dimethylformamide / 6 h / 20 °C

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: Me₂S / methanol; CH₂Cl₂ / 3 h / -78 - 20 °C

3.1: 142 mg / CeCl₃*H₂O; NaBH₄ / methanol / 0 - 20 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

4.2: tetrahydrofuran / 1 h / 20 °C

4.3: 66 mg / tetrahydrofuran / 0.5 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(03)00532-9