Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Base Information

Chemical Name:Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester
CAS No.:114826-63-0
Molecular Formula:C₂₉H₃₁N₃O₈S
Molecular Weight:581.646
Hs Code.:

Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

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Chemical Property of Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

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Technology Process of Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

There total 4 articles about Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-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: 96.0%

: 114826-61-8,114826-62-9
Benzoic acid (2R,4aS,7S,8R,8aS)-7-tert-butoxycarbonylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 114826-63-0,114826-64-1
Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Guidance literature:: In 1,2-dichloro-ethane; for 2.5h; Heating;
DOI:10.1016/S0040-4039(00)96878-3

Reference yield:

: ((3S,4R,5S,6S)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

: 114826-63-0,114826-64-1
Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / ZnCl₂ / 4 h / Ambient temperature

2: 76 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C upto RT

3: 96 percent / 1,2-dichloro-ethane / 2.5 h / Heating

With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(00)96878-3

Reference yield:

: ((2R,4aS,7S,8R,8aS)-6,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid tert-butyl ester

: 114826-63-0,114826-64-1
Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C upto RT

2: 96 percent / 1,2-dichloro-ethane / 2.5 h / Heating

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(00)96878-3