Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

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Chemical Name:Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester
CAS No.:1054647-37-8
Molecular Formula:C₂₉H₃₉F₃O₇SSi
Molecular Weight:616.771
Hs Code.:

Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

Synonyms:Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

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Chemical Property of Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

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Technology Process of Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

There total 13 articles about Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl 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:

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 1-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-one

: 1054647-37-8
Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 0 ℃; for 0.666667h;
DOI:10.1021/ol015798l

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1054647-37-8
Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

1.2: 85 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

2.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

3.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

4.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

4.2: 95 percent / NaHCO₃; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

5.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / 0 °C

6.1: tetrahydrofuran; diethyl ether / 0.58 h / -78 - 0 °C

7.1: 4.64 g / TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / CH₂Cl₂ / 3 h / 20 °C

8.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; sodium hexamethyldisilazane; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 3.1: Wittig reaction / 6.1: Grignard reaction;
DOI:10.1021/ol015798l

Reference yield:

: 100-39-0
benzyl bromide

: 1054647-37-8
Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

2.1: 1.63 g / CSA / CH₂Cl₂; methanol / 20 h / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

3.2: 85 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

4.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

5.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

6.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

6.2: 95 percent / NaHCO₃; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

7.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / 0 °C

8.1: tetrahydrofuran; diethyl ether / 0.58 h / -78 - 0 °C

9.1: 4.64 g / TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / CH₂Cl₂ / 3 h / 20 °C

10.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 5.1: Wittig reaction / 8.1: Grignard reaction;
DOI:10.1021/ol015798l