Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester
• CAS No.: 138794-98-6
• Molecular Formula: C₂₂H₄₈O₈SSi₂
• Molecular Weight: 528.855
• Mol file: 138794-98-6.mol

Synonyms:Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester

Chemical Property of Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester

There total 14 articles about Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl 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:

(1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane (128184-69-0,134680-61-8) → Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester (138794-98-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol;

DOI:10.1016/S0040-4039(00)88756-0

Reference yield:

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran (128184-62-3) → Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester (138794-98-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) dicyclohexylborane, 2) 3M aq. NaOH, 30percent H₂O₂ / 1) THF, 25 deg C, 1.5h, 2) H₂O, 50 deg C, 20 min

2: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

3: 75 percent / benzene / 0.25 h / 25 °C

4: 83 percent / 1,2M aq. HCl / dioxane / 12 h / 80 °C

5: 96 percent / H₂NOH*HCl, pyridine / 2 h / 25 °C

6: 70 percent / 5percent aq. NaOCl / CH₂Cl₂ / 1.5 h / 25 °C

7: 80 percent / H₂, HOAc / Raney-Ni-W₄ / H₂O; dioxane / 1.5 h / 25 °C / 760 Torr

8: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: 60 percent / BH₃*Me₂S / tetrahydrofuran / 12 h / 25 °C

10: 80 percent / pyridine / 12 h / 25 °C

11: 9.0 mg / H₂ / Pd(OH)2 / methanol / 0.5 h / 25 °C / 760 Torr

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium hypochlorite; oxalyl dichloride; dimethylsulfide borane complex; bis(cyclohexanyl)borane; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; acetic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; Raney-Ni-W₄; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; benzene;

DOI:10.1016/0008-6215(91)89017-A

Reference yield:

methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside (128184-64-5) → Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester (138794-98-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / 1,2M aq. HCl / dioxane / 12 h / 80 °C

2: 96 percent / H₂NOH*HCl, pyridine / 2 h / 25 °C

3: 70 percent / 5percent aq. NaOCl / CH₂Cl₂ / 1.5 h / 25 °C

4: 80 percent / H₂, HOAc / Raney-Ni-W₄ / H₂O; dioxane / 1.5 h / 25 °C / 760 Torr

5: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 60 percent / BH₃*Me₂S / tetrahydrofuran / 12 h / 25 °C

7: 80 percent / pyridine / 12 h / 25 °C

8: 9.0 mg / H₂ / Pd(OH)2 / methanol / 0.5 h / 25 °C / 760 Torr

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium hypochlorite; dimethylsulfide borane complex; hydroxylamine hydrochloride; hydrogen; acetic acid; palladium dihydroxide; Raney-Ni-W₄; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/0008-6215(91)89017-A

upstream raw materials:

(1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane

diethyl(isopropyl)silyl trifluoromethanesulfonate

methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran

Downstream raw materials:

cyclophellitol