(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

Base Information

• Chemical Name: (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
• CAS No.: 90941-98-3
• Molecular Formula: C₃₇H₅₈O₈SSi
• Molecular Weight: 691.014
• Mol file: 90941-98-3.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 28 articles about (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 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:

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol (90941-89-2) → (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 (90941-98-3,90988-95-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / Ti(O-i-Pr)4, diethyl (-)-tartrate, TBHP / CH₂Cl₂ / -20 °C

2: 76 percent / Redal / tetrahydrofuran / -20 °C

3: 65 percent / NaH / hexamethylphosphoric acid triamide; dimethylformamide / Ambient temperature

4: 100 percent / 0.8percent H₂SO₄ / methanol / Ambient temperature

5: 85 percent / imidazole / tetrahydrofuran / Ambient temperature

6: 98 percent / CSA catalyst / acetone / Ambient temperature

7: 98 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

8: 88 percent / NaH, 18-crown-6 / tetrahydrofuran / 0 deg C -> rt

9: 97 percent / n-Bu₄NF / tetrahydrofuran / 0 °C

10: 91 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / -20 °C

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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 2,6-di-tert-butyl-pyridine; 18-crown-6 ether; diethyl (2S,3S)-tartrate; sulfuric acid; tetrabutyl ammonium fluoride; sodium; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; CSA catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00189a046

Reference yield:

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid ethyl ester → (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 (90941-98-3,90988-95-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / Dibal / tetrahydrofuran / -40 °C

2: 77 percent / Ti(O-i-Pr)4, diethyl (-)-tartrate, TBHP / CH₂Cl₂ / -20 °C

3: 76 percent / Redal / tetrahydrofuran / -20 °C

4: 65 percent / NaH / hexamethylphosphoric acid triamide; dimethylformamide / Ambient temperature

5: 100 percent / 0.8percent H₂SO₄ / methanol / Ambient temperature

6: 85 percent / imidazole / tetrahydrofuran / Ambient temperature

7: 98 percent / CSA catalyst / acetone / Ambient temperature

8: 98 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

9: 88 percent / NaH, 18-crown-6 / tetrahydrofuran / 0 deg C -> rt

10: 97 percent / n-Bu₄NF / tetrahydrofuran / 0 °C

11: 91 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / -20 °C

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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; 2,6-di-tert-butyl-pyridine; 18-crown-6 ether; diethyl (2S,3S)-tartrate; sulfuric acid; tetrabutyl ammonium fluoride; sodium; sodium hydride; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; CSA catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00189a046

Reference yield:

[(2R,3R)-3-((S)-2,2-Diethyl-[1,3]dioxolan-4-ylmethyl)-oxiranyl]-methanol (90941-90-5) → (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 (90941-98-3,90988-95-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 76 percent / Redal / tetrahydrofuran / -20 °C

2: 65 percent / NaH / hexamethylphosphoric acid triamide; dimethylformamide / Ambient temperature

3: 100 percent / 0.8percent H₂SO₄ / methanol / Ambient temperature

4: 85 percent / imidazole / tetrahydrofuran / Ambient temperature

5: 98 percent / CSA catalyst / acetone / Ambient temperature

6: 98 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

7: 88 percent / NaH, 18-crown-6 / tetrahydrofuran / 0 deg C -> rt

8: 97 percent / n-Bu₄NF / tetrahydrofuran / 0 °C

9: 91 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / -20 °C

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

With 1H-imidazole; n-butyllithium; 2,6-di-tert-butyl-pyridine; 18-crown-6 ether; sulfuric acid; tetrabutyl ammonium fluoride; sodium; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; CSA catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00189a046

upstream raw materials:

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

Trifluoro-methanesulfonic acid (4S,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl ester

(E)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol

(S)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-butane-1,3-diol

Downstream raw materials:

(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