Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Name:Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:256341-87-4
Molecular Formula:C₂₀H₂₂Cl₃NO₆
Molecular Weight:478.757
Hs Code.:

Synonyms:Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl 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: 85.0%

: 545-06-2
trichloroacetonitrile

: Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-hydroxy-tetrahydro-pyran-3-yl ester

: 256341-87-4
Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 25 ℃; for 0.5h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

: 306726-12-5
Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester

: 256341-87-4
Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

2.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

3.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

4.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; acetonitrile; 1.1: Methylation / 2.1: Reduction / 2.2: Ring cleavage / 3.1: Cyclization / 4.1: Addition;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 306726-10-3
(1R,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol

: 256341-87-4
Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

3.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

4.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

5.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; acetonitrile; 1.1: Esterification / 2.1: Methylation / 3.1: Reduction / 3.2: Ring cleavage / 4.1: Cyclization / 5.1: Addition;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8