Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester
• CAS No.: 127723-93-7
• Molecular Formula: C₄₂H₅₈O₇S₂Si
• Molecular Weight: 767.136

Synonyms:

Chemical Property of Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester

There total 21 articles about Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) 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:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3,147220-48-2,116996-54-4) → Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester (127723-93-7,127760-91-2)

Guidance literature:

Multi-step reaction with 9 steps

2: 97 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 76 percent / n-BuLi, HMPA / tetrahydrofuran / -78 °C

4: aq. AcOH

5: CSA / CH₂Cl₂ / Ambient temperature

6: NBS, AgNO₃, 2,6-lutidine / acetonitrile; H₂O

7: 80 percent / K₂CO₃ / methanol

8: DIBAH / toluene / -48 °C

9: NaH / tetrahydrofuran

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; silver nitrate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)89012-2

Reference yield:

benzyl bromide (100-39-0) → Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester (127723-93-7,127760-91-2)

Guidance literature:

Multi-step reaction with 10 steps

3: 98 percent / Et₃N / Ambient temperature

4: 74 percent / Et₃N

5: aq. AcOH

6: CSA / CH₂Cl₂

7: 52 percent / t-BuONa, KMnO₄ / 2-methyl-propan-2-ol

8: 80 percent / K₂CO₃ / methanol

9: DIBAH / toluene / -48 °C

10: NaH / tetrahydrofuran

With potassium permanganate; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; sodium t-butanolate; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)89012-2

Reference yield:

(2R)-2-(2-benzyloxyethyl)oxirane (115114-87-9) → Dithiocarbonic acid O-([(4R,6R)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methyl) ester S-methyl ester (127723-93-7,127760-91-2)

Guidance literature:

Multi-step reaction with 9 steps

2: 98 percent / Et₃N / Ambient temperature

3: 74 percent / Et₃N

4: aq. AcOH

5: CSA / CH₂Cl₂

6: 52 percent / t-BuONa, KMnO₄ / 2-methyl-propan-2-ol

7: 80 percent / K₂CO₃ / methanol

8: DIBAH / toluene / -48 °C

9: NaH / tetrahydrofuran

With potassium permanganate; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; sodium t-butanolate; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)89012-2

upstream raw materials:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

benzyl bromide

(2R)-2-(2-benzyloxyethyl)oxirane

(R)-6-Benzyloxy-1-nitro-4-(tetrahydro-pyran-2-yloxy)-hexan-2-ol

Downstream raw materials:

(2-{(4S,6S)-6-[(4R,6R)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethoxy)-tert-butyl-diphenyl-silane

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