5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

Base Information

Chemical Name:5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol
CAS No.:651718-91-1
Molecular Formula:C₃₀H₄₉F₂N₂O₅PS₂Si
Molecular Weight:678.918
Hs Code.:

5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

Synonyms:5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

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Chemical Property of 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

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Technology Process of 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

There total 4 articles about 5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol 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: 40.0%

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

: 651718-77-3
5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-1-O-(triisopropylsilyl)-D-erythro-pentitol

: (4S,5S)-5-[(benzyloxy)methyl]-2-ethoxy-3,3-difluoro-4-{2-[(triisopropylsilyl)oxy]ethyl}-1,2-oxaphospholane 2-sulfide

: 651718-91-1
5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

Guidance literature:: In tetrahydrofuran; at 65 ℃; for 15h;
DOI:10.1016/j.tet.2003.10.064

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 651718-91-1
5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: 35 percent / tetrahydrofuran / 15 h / 65 °C

With 2,6-dimethylpyridine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2003.10.064

Reference yield:

: 651718-75-1
(2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

: 651718-91-1
5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / LiBH₄; B(OMe)3 / tetrahydrofuran / 8 h / 20 °C

2: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3: 35 percent / tetrahydrofuran / 15 h / 65 °C

With 2,6-dimethylpyridine; lithium borohydride; Trimethyl borate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2003.10.064