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

Base Information

• Chemical Name: Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexyl ester
• CAS No.: 128184-69-0
• Molecular Formula: C₄₃H₆₆O₈SSi₂
• Molecular Weight: 799.229
• Mol file: 128184-69-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 26 articles about Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-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: 95.0%

(1R,2S,3S,4R,5R,6S)-2,3,4-tribenzyloxy-5-<(1-methylethyl)diethylsilyl>oxy-6-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexanol (128184-68-9,134680-60-7,138875-25-9) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexyl ester (128184-69-0,134680-61-8)

Guidance literature:

With pyridine; at 25 ℃; for 12h;

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

Reference yield: 80.0%

(1S,2R,3S,4R,5R,6S)-2,3,4-tribenzyloxy-5-<(1-methylethyl)diethylsilyl>oxy-6-<<(1-methylethyl)diethylsilyl>oxymethyl>cyclohexanol (128184-68-9) + methanesulfonyl chloride (124-63-0) → (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)

Guidance literature:

With pyridine; at 25 ℃; for 12h;

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

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4) → Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexyl ester (128184-69-0,134680-61-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 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

2: 91 percent / benzene / 0.17 h / 25 °C

3: 1) Ac₂O, conc. H₂SO₄, 2) NaOMe / 1) 0 deg C, 10 min, 2a) MeOH, 0 deg c, 10 min, 2b) 25 deg C, 0.5h

4: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

5: 75 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C

6: 28 percent / H₂, HOAc / Raney-Ni-W₄ / H₂O; dioxane / 4 h / 25 °C / 760 Torr

7: 65 percent / NEt₃ / CH₂Cl₂ / 48 h / 25 °C

8: 80 percent / BH₃*Me₂S / tetrahydrofuran / 0.5 h / 0 °C

9: 39 percent / imidazole / dimethylformamide / 4 h / 0 °C

10: 60 percent / imidazole / dimethylformamide / 0 °C

11: 95 percent / pyridine / 12 h / 25 °C

With pyridine; 1H-imidazole; sodium hypochlorite; oxalyl dichloride; hydrazine hydrochloride; dimethylsulfide borane complex; sulfuric acid; hydrogen; sodium methylate; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; Raney-Ni-W₄; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

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

upstream raw materials:

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

methanesulfonyl chloride

diethyl(isopropyl)silyl trifluoromethanesulfonate

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

Downstream raw materials:

(1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol

(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate

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