(2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran
• CAS No.: 380578-98-3
• Molecular Formula: C₅₆H₉₄O₈SSi₄
• Molecular Weight: 1039.77
• Mol file: 380578-98-3.mol

Synonyms:(2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran

Chemical Property of (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran

There total 15 articles about (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran 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:

2,2-dimethyl-3-(phenylsulfonyl)propanoic acid (38435-02-8) → (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran (380578-98-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: K₂CO₃ / dimethylformamide / 12 h / 20 °C

2.1: 65 percent / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

3.1: LiCl; i-Pr₂NEt / acetonitrile / 16 h / 20 °C

4.1: H₂ / Pd(OH)2/C / methanol / 2 h / 20 °C

5.1: 84 percent / camphorsulfonic acid / benzene / 2 h / Heating

6.1: dimethyldioxirane; 4 Angstroem molecular sieves / acetone; methanol / 0.2 h / 0 °C

6.2: PPTS; 4 Angstroem molecular sieves / acetone / 0.17 h / 20 °C

7.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

8.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C

9.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.08 h / -78 - 0 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 3.1: Horner-Wadsworth-Emmons reaction / 9.1: Luche reduction;

DOI:10.1021/ol016800b

Reference yield:

2-Phenylthiomethyl-2-methyl-1-propanol (51916-36-0) → (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran (380578-98-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 89 percent / oxone / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

2.1: RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O / 2 h / 0 - 20 °C

3.1: K₂CO₃ / dimethylformamide / 12 h / 20 °C

4.1: 65 percent / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

5.1: LiCl; i-Pr₂NEt / acetonitrile / 16 h / 20 °C

6.1: H₂ / Pd(OH)2/C / methanol / 2 h / 20 °C

7.1: 84 percent / camphorsulfonic acid / benzene / 2 h / Heating

8.1: dimethyldioxirane; 4 Angstroem molecular sieves / acetone; methanol / 0.2 h / 0 °C

8.2: PPTS; 4 Angstroem molecular sieves / acetone / 0.17 h / 20 °C

9.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

10.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C

11.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.08 h / -78 - 0 °C

12.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; ruthenium trichloride; Oxone; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 5.1: Horner-Wadsworth-Emmons reaction / 11.1: Luche reduction;

DOI:10.1021/ol016800b

Reference yield:

3-Benzenesulfonyl-2,2-dimethyl-propionic acid methyl ester (38434-99-0) → (2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-3-triethylsilanyloxy-tetrahydro-pyran (380578-98-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 65 percent / n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

2.1: LiCl; i-Pr₂NEt / acetonitrile / 16 h / 20 °C

3.1: H₂ / Pd(OH)2/C / methanol / 2 h / 20 °C

4.1: 84 percent / camphorsulfonic acid / benzene / 2 h / Heating

5.1: dimethyldioxirane; 4 Angstroem molecular sieves / acetone; methanol / 0.2 h / 0 °C

5.2: PPTS; 4 Angstroem molecular sieves / acetone / 0.17 h / 20 °C

6.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

7.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C

8.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1.08 h / -78 - 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; 3,3-dimethyldioxirane; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 2.1: Horner-Wadsworth-Emmons reaction / 8.1: Luche reduction;

DOI:10.1021/ol016800b

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(2S,3S,6S)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-6-[(2R,3R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-methoxy-tetrahydro-pyran-3-ol

2-Phenylthiomethyl-2-methyl-1-propanol

2,2-dimethyl-3-(phenylsulfonyl)propanoic acid