dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

Base Information

Chemical Name:dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate
CAS No.:873550-81-3
Molecular Formula:C₂₁H₂₆N₃O₆P
Molecular Weight:447.428
Hs Code.:

Synonyms:dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

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Technology Process of dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

There total 5 articles about dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate 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: 59.0%

: 873550-72-2
(2S,3S)-4-azido-2,3-O-isopropylidene-2,3-dihydroxybutanal

: 17176-77-1
Dibenzyl phosphite

: 873550-79-9
dibenzyl (1S,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

: 873550-81-3
dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

Guidance literature:: With triethylamine; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2005.09.057

Reference yield:

: 59779-75-8
diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

: 873550-81-3
dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 20 h / 20 °C

2: Ag₂O; KI / CH₂Cl₂ / 2 h / 20 °C

3: 94 percent / NaN₃ / dimethylformamide / 24 h / 80 °C

4: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 0 °C

5: 24 percent / Et₃N / 24 h / 20 °C

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; potassium iodide; lithium chloride; silver(l) oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;
DOI:10.1016/j.tet.2005.09.057

Reference yield:

: 50622-09-8
2,3-O-isopropylidene-L-threitol

: 873550-81-3
dibenzyl (1R,2R,3S)-4-azido-1,2,3-trihydroxy-2,3-O-isopropylidenebutylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1: Ag₂O; KI / CH₂Cl₂ / 2 h / 20 °C

2: 94 percent / NaN₃ / dimethylformamide / 24 h / 80 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 0 °C

4: 24 percent / Et₃N / 24 h / 20 °C

With sodium azide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1016/j.tet.2005.09.057