3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Base Information

Chemical Name:3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose
CAS No.:225233-53-4
Molecular Formula:C₂₄H₂₂O₇
Molecular Weight:422.434
Hs Code.:

Synonyms:3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

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Chemical Property of 3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

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Technology Process of 3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

There total 10 articles about 3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose 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: 72.0%

: 98-88-4
benzoyl chloride

: 225233-51-2
4-C-ethynyl-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-α-D-ribo-pentofuranose

: 225233-53-4
3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: 4-C-ethynyl-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-α-D-ribo-pentofuranose; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; at 20 ℃; for 24h;

benzoyl chloride; With pyridine; at 20 ℃; for 2h;
DOI:10.1271/bbb.63.736

Reference yield:

: C₁₇H₁₈O₆

: 98-88-4
benzoyl chloride

: 225233-53-4
3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: With pyridine; at 20 ℃; for 3h;

Reference yield:

: 69940-04-1,142226-16-2,109536-51-8
(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

: 225233-53-4
3,5-di-O-benzoyl-4-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaIO₄ / H₂O / 1.5 h / 20 °C

2.1: NaOH / H₂O; tetrahydrofuran / 46 h / 20 °C

3.1: 66 percent / NaH / dimethylformamide / 6 h / -20 °C

4.1: 76 percent / pyridinium dichromate / dimethylformamide / 10 h / 40 °C

5.1: 95 percent / Ph₃P / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

7.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / methanol; CH₂Cl₂ / 24 h / 20 °C

7.2: 72 percent / Py / 2 h / 20 °C

With sodium hydroxide; sodium periodate; dipyridinium dichromate; n-butyllithium; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Condensation / 3.1: Alkylation / 4.1: Oxidation / 5.1: Condensation / 6.1: Dehydrobromination / 7.1: Substitution / 7.2: Acylation;
DOI:10.1271/bbb.63.736