(2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone

Base Information

• Chemical Name: (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone
• CAS No.: 138794-97-5
• Molecular Formula: C₄₂H₆₂O₆Si₂
• Molecular Weight: 719.122
• Mol file: 138794-97-5.mol

Synonyms:(2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone

Chemical Property of (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone

There total 10 articles about (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone 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%

diethyl(isopropyl)silyl trifluoromethanesulfonate (126889-55-2) + (2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone (128184-67-8) → (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone (138794-97-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;

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

Reference yield:

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran (128184-62-3) → (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone (138794-97-5)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium hypochlorite; oxalyl dichloride; bis(cyclohexanyl)borane; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; acetic acid; dimethyl sulfoxide; triethylamine; Raney-Ni-W₄; In 1,4-dioxane; 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) → (2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone (138794-97-5)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium hypochlorite; hydroxylamine hydrochloride; hydrogen; acetic acid; Raney-Ni-W₄; In 1,4-dioxane; dichloromethane; water;

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

upstream raw materials:

diethyl(isopropyl)silyl trifluoromethanesulfonate

(2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

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:

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

(1R,2R,3S,4R,5R,6S)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanol

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

(2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone