Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester
• CAS No.: 116726-62-6
• Molecular Formula: C₃₂H₄₆O₇SSi
• Molecular Weight: 602.865

Synonyms:Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester

Chemical Property of Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester

There total 10 articles about Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-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: 100.0%

methanesulfonyl chloride (124-63-0) + (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol (116726-61-5) → Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester (116726-62-6)

Guidance literature:

With triethylamine; In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1021/jo00260a016

Reference yield:

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose (35784-67-9) → Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester (116726-62-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) KH / 1.) THF, RT, 1 h, 2.) reflux, 8 h

2: 90 percent / 90percent AcOH / 4 h / 60 °C

3: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

4: 88 percent / tetrahydrofuran / 3 h

5: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

6: 79 percent / DIBAL / toluene / 1 h / -78 °C

7: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

9: 100 percent / triethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

With lead(IV) acetate; Celite; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1021/jo00260a016

Reference yield:

(R)-1-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol (116726-54-6) → Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester (116726-62-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

2: 88 percent / tetrahydrofuran / 3 h

3: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

4: 79 percent / DIBAL / toluene / 1 h / -78 °C

5: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

7: 100 percent / triethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

With lead(IV) acetate; Celite; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1021/jo00260a016

upstream raw materials:

methanesulfonyl chloride

(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

3-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propionaldehyde

Downstream raw materials:

(Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

(Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-4-methyl-hept-4-enenitrile

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