Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester
• CAS No.: 136061-53-5
• Molecular Formula: C₃₃H₅₄O₇S₂Si
• Molecular Weight: 655.005
• Mol file: 136061-53-5.mol

Synonyms:

Chemical Property of Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester

There total 19 articles about Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl 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:

O1,O2;O5,O6-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose (21665-16-7) → Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester (136061-53-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / H₂, Et₃N / 10percent Pd/C / methanol / 5 h / 22 °C

2: 84 percent / 0.1 N H₂SO₄ / methanol / 5 h / 22 °C

3: 1) NaIO₄, 2) NaBH₄ / 1) C₂H₅OH/H₂O, 5 deg C, 30 min, 2) 5 deg C, 30 min

4: 88 percent / pyridine / 2 h / 22 °C

5: 79 percent / conc. HCl / 6 h / 0 °C

6: 92 percent / p-TsOH / acetone / 2 h / 22 °C

7: 93 percent / CH₃I, CdCO₃ / acetone; H₂O / 24 h / 22 °C

8: 71 percent / NaNH₂ / tetrahydrofuran / 2 h / 22 °C

9: 83 percent / 0.1 N NaOH / methanol / 3 h / 22 °C

10: 1) (COCl)2, 2) EtNi-Pr₂ / 1) DMSO, CH₂Cl₂, -78 deg C, 15 min

11: 1) nBuLi / 1) THF, -78 deg C, 1 h, 2) 22 deg C, 90 min

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; sulfuric acid; hydrogen; toluene-4-sulfonic acid; sodium amide; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetone;

Reference yield:

(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol (26291-75-8,81114-49-0,109200-09-1,128461-80-3) → Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester (136061-53-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) NaIO₄, 2) NaBH₄ / 1) C₂H₅OH/H₂O, 5 deg C, 30 min, 2) 5 deg C, 30 min

2: 88 percent / pyridine / 2 h / 22 °C

3: 79 percent / conc. HCl / 6 h / 0 °C

4: 92 percent / p-TsOH / acetone / 2 h / 22 °C

5: 93 percent / CH₃I, CdCO₃ / acetone; H₂O / 24 h / 22 °C

6: 71 percent / NaNH₂ / tetrahydrofuran / 2 h / 22 °C

7: 83 percent / 0.1 N NaOH / methanol / 3 h / 22 °C

8: 1) (COCl)2, 2) EtNi-Pr₂ / 1) DMSO, CH₂Cl₂, -78 deg C, 15 min

9: 1) nBuLi / 1) THF, -78 deg C, 1 h, 2) 22 deg C, 90 min

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; toluene-4-sulfonic acid; sodium amide; N-ethyl-N,N-diisopropylamine; methyl iodide; In tetrahydrofuran; methanol; water; acetone;

Reference yield:

(3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,6-trimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (26293-58-3) → Acetic acid (E)-(3R,4S)-2-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-1-[(4S,5S,6R)-2,2,5-trimethyl-6-((Z)-2-methylsulfanyl-vinyl)-[1,3]dioxan-4-yl]-hept-5-enyl ester (136061-53-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / 0.1 N H₂SO₄ / methanol / 5 h / 22 °C

2: 1) NaIO₄, 2) NaBH₄ / 1) C₂H₅OH/H₂O, 5 deg C, 30 min, 2) 5 deg C, 30 min

3: 88 percent / pyridine / 2 h / 22 °C

4: 79 percent / conc. HCl / 6 h / 0 °C

5: 92 percent / p-TsOH / acetone / 2 h / 22 °C

6: 93 percent / CH₃I, CdCO₃ / acetone; H₂O / 24 h / 22 °C

7: 71 percent / NaNH₂ / tetrahydrofuran / 2 h / 22 °C

8: 83 percent / 0.1 N NaOH / methanol / 3 h / 22 °C

9: 1) (COCl)2, 2) EtNi-Pr₂ / 1) DMSO, CH₂Cl₂, -78 deg C, 15 min

10: 1) nBuLi / 1) THF, -78 deg C, 1 h, 2) 22 deg C, 90 min

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; sulfuric acid; toluene-4-sulfonic acid; sodium amide; N-ethyl-N,N-diisopropylamine; methyl iodide; In tetrahydrofuran; methanol; water; acetone;

upstream raw materials:

acetic anhydride

(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,6-trimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose