Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 137271-78-4
• Molecular Formula: C₁₄H₂₃F₃O₅S
• Molecular Weight: 360.395

Synonyms:Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 5 articles about Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (137271-78-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaBH₄, 2) NaIO₄ / 1) 0 deg C, 2h, 2) RT, 2h

2: tetrahydrofuran / 1) -30 deg C, 0.5h, 2) RT, 7h

3: H₂ / Raney Ni / ethanol

4: pyridine / 0.25 h / -15 °C

With pyridine; sodium tetrahydroborate; sodium periodate; hydrogen; nickel; In tetrahydrofuran; ethanol;

DOI:10.1016/0040-4039(91)80024-Z

Reference yield:

cyclohexyltriphenylphosphorane (16666-81-2) → Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (137271-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1) -30 deg C, 0.5h, 2) RT, 7h

2: H₂ / Raney Ni / ethanol

3: pyridine / 0.25 h / -15 °C

With pyridine; hydrogen; nickel; In tetrahydrofuran; ethanol;

DOI:10.1016/0040-4039(91)80024-Z

Reference yield:

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) → Trifluoro-methanesulfonic acid (4S,5R)-5-cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (137271-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1) -30 deg C, 0.5h, 2) RT, 7h

2: H₂ / Raney Ni / ethanol

3: pyridine / 0.25 h / -15 °C

With pyridine; hydrogen; nickel; In tetrahydrofuran; ethanol;

DOI:10.1016/0040-4039(91)80024-Z

upstream raw materials:

trifluoromethylsulfonic anhydride

((4S,5R)-5-Cyclohexylmethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

2,3-O-isopropylidene-L-erythrofuranose

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(S)-5-((R)-2-Cyclohexyl-1-hydroxy-ethyl)-dihydro-furan-2-one

(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

Methanesulfonic acid (R)-2-cyclohexyl-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

(5S,1'S)-5-(1'-azido-2'-cyclohexylethyl)dihydrofuran-2(3H)-one

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