Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester
• CAS No.: 145345-66-0
• Molecular Formula: C₁₉H₂₄O₇S
• Molecular Weight: 396.461
• Mol file: 145345-66-0.mol

Synonyms:

Chemical Property of Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester

There total 1 articles about Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl 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: 88.0%

phenylcarbonochloridothioate (1005-56-7) + 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose (582-52-5,2595-05-3,10368-86-2,13100-30-6,14686-89-6,23262-79-5,26597-74-0,26623-15-4,38166-58-4,38166-60-8,79943-22-9,83730-28-3) → Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (19189-62-9,145345-66-0)

Guidance literature:

With dmap; In acetonitrile; 0 deg C -> rt;

DOI:10.1021/jo00189a046

Reference yield:

Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (19189-62-9,145345-66-0) → (R)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol (90941-83-6,90988-93-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 95 percent / n-Bu₃SnH, AlBN / benzene / 80 °C

2: aq. 0.8percent H₂SO₄ / methanol / Ambient temperature

3: tetrahydrofuran / Ambient temperature

4: Dowex-50 acidic resin / H₂O; benzene / 50 °C

5: NaBH₄ / methanol; H₂O / 0 °C

6: 74 percent / imidazole / tetrahydrofuran / -20 °C

7: 92 percent / p-TsOH / acetone / Ambient temperature

8: 100 percent / K₂CO₃ / methanol / Ambient temperature

9: 77 percent / Et₃N / acetonitrile / -10 °C

10: 1) MsCl, Et₃N, 2) n-Bu₄NOH / 1) Et₂O, 0 deg C, 2) Et₂O, MeOH (trace), rt

11: 91 percent / aq. 0.5 N NaOH / tetrahydrofuran / 0 deg C -> rt

12: 87 percent / NaIO₄ / methanol; H₂O / 0 °C

13: 1) n-BuLi / 1) THF, HMPA, -30 deg C, 1 h, 2) -30 deg C -> -20 deg C

14: 86 percent / Raney nickel / acetone / Ambient temperature

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); Dowex-50 acidic resin; sulfuric acid; tetra(n-butyl)ammonium hydroxide; tri-n-butyl-tin hydride; nickel; potassium carbonate; methanesulfonyl chloride; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; acetonitrile; benzene;

DOI:10.1021/jo00189a046

Reference yield:

Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (19189-62-9,145345-66-0) → (S)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol (90941-83-6,90988-93-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / n-Bu₃SnH, AlBN / benzene / 80 °C

2: aq. 0.8percent H₂SO₄ / methanol / Ambient temperature

3: tetrahydrofuran / Ambient temperature

4: Dowex-50 acidic resin / H₂O; benzene / 50 °C

5: NaBH₄ / methanol; H₂O / 0 °C

6: 74 percent / imidazole / tetrahydrofuran / -20 °C

7: 92 percent / p-TsOH / acetone / Ambient temperature

8: 100 percent / K₂CO₃ / methanol / Ambient temperature

9: 96 percent / NaIO₄ / methanol; H₂O / Ambient temperature

10: 1) n-BuLi, i-Pr₂NH / 1) THF, -60 deg C, 2) -78 deg C

11: Raney-Nickel / acetone / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); Dowex-50 acidic resin; sulfuric acid; tri-n-butyl-tin hydride; nickel; potassium carbonate; diisopropylamine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; benzene;

DOI:10.1021/jo00189a046

upstream raw materials:

phenylcarbonochloridothioate

1,2:5,6-di-O-isopropylidene-α-L-glucofuranose

Downstream raw materials:

(S)-2-Benzenesulfinyl-3-[(4S,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol

(S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol

(R)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol

(S)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol