Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Name:Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester
CAS No.:157189-70-3
Molecular Formula:C₂₁H₂₆O₈S
Molecular Weight:438.499
Hs Code.:

Synonyms:Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Chemical Property of Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

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Technology Process of Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

There total 9 articles about Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-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: 83.0%

: Acetic acid (1R,2R)-2-acetoxy-1-[(S)-6-hydroxy-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

: 157189-70-3
Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: With jones reagent; 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

: 157189-70-3
Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 9 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

8: 1.) Br₂, 2.) K₂CO₃, 3.) NaOMe

9: 83 percent / Jones reagent / 1 h / 0 °C

With jones reagent; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; bromine; sodium methylate; 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

: 157189-70-3
Acetic acid (1S,2R)-2-acetoxy-1-[(S)-6-oxo-4-(toluene-4-sulfonyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 1.) Br₂, 2.) K₂CO₃, 3.) NaOMe

7: 83 percent / Jones reagent / 1 h / 0 °C

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