Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Name:Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester
CAS No.:157189-68-9
Molecular Formula:C₂₁H₂₈O₇S
Molecular Weight:424.515
Hs Code.:

Synonyms:Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Property of Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

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Technology Process of Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

There total 7 articles about Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl 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: 81.0%

: 108-24-7
acetic anhydride

: 157189-63-4
(R)-1-[(1S,3R,5S,7S)-3-(Toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]oct-7-yl]-butan-1-ol

: 157189-68-9
Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1248/cpb.42.179

Reference yield:

: 89927-11-7,127757-94-2
7-mesyloxymethyl-3-tosyl-6,8-dioxabicyclo<3.2.1>octane

: 157189-68-9
Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / 18-crown-6 / dimethylformamide / 12 h / 80 °C

2: 86 percent / K₂CO₃ / methanol / 12 h / Ambient temperature

3: 85 percent / (COCl)2, DMSO, Et₃N / 5 h / -78 - 0 °C

4: 88 percent / tetrahydrofuran / 1 h / 0 °C

5: 87 percent / Jones reagent / 1 h / 0 °C

6: 100 percent / L-Selectride / tetrahydrofuran / 2 h / -78 °C

7: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

With jones reagent; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; L-Selectride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.179

Reference yield:

: [(1S,3R,5S,7S)-3-(Toluene-4-sulfonyl)-6,8-dioxa-bicyclo[3.2.1]oct-7-yl]-methanol

: 157189-68-9
Acetic acid (1R,2R)-2-acetoxy-1-[(2S,4R)-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / (COCl)2, DMSO, Et₃N / 5 h / -78 - 0 °C

2: 88 percent / tetrahydrofuran / 1 h / 0 °C

3: 87 percent / Jones reagent / 1 h / 0 °C

4: 100 percent / L-Selectride / tetrahydrofuran / 2 h / -78 °C

5: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

With jones reagent; oxalyl dichloride; boron trifluoride diethyl etherate; L-Selectride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.42.179