Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 529488-04-8
• Molecular Formula: C₂₄H₃₁F₃O₆SSi
• Molecular Weight: 532.653

Synonyms:Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-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: 96.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8)

Guidance literature:

With pyridine; In dichloromethane; at -12 ℃; for 0.25h;

DOI:10.1039/b209637b

Reference yield: 59.0%

4-bromo-2-methylbenzofuran (219739-70-5) + Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8) → {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-06-0)

Guidance literature:

4-bromo-2-methylbenzofuran; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 1h;

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester; With copper(I) bromide; In tetrahydrofuran; at 0 ℃; for 14h; Further stages.;

DOI:10.1039/b209637b

Reference yield:

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8) → 2-[(2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

1.2: 59 percent / CuBr / tetrahydrofuran / 14 h / 0 °C

2.1: O₃/O₂ / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 68 percent / PPh₃; O₂ / CH₂Cl₂ / 4 h / -78 - 20 °C

3.1: 94 percent / NaClO₂; NaHSO₃; aq. H₂O₂ / NaH₂PO₄ / acetonitrile / 3.5 h / 20 °C

4.1: K₂CO₃ / methanol / 1 h / 20 °C

With sodium chlorite; dihydrogen peroxide; iodine; oxygen; potassium carbonate; ozone; sodium hydrogensulfite; magnesium; sodium dihydrogenphosphate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1039/b209637b

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Downstream raw materials:

{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

{(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid

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