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

Base Information

Chemical Name:4-C-ethynyl-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-α-D-ribo-pentofuranose
CAS No.:225233-51-2
Molecular Formula:C₂₆H₃₀O₇
Molecular Weight:454.52
Hs Code.:

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

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

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

There total 9 articles about 4-C-ethynyl-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-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: 92.0%

: 225233-50-1
4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-α-D-ribo-pentofuranose

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

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1271/bbb.63.736

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

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

Guidance literature:: Multi-step reaction with 6 steps

1: NaIO₄ / H₂O / 1.5 h / 20 °C

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

3: 66 percent / NaH / dimethylformamide / 6 h / -20 °C

4: 76 percent / pyridinium dichromate / dimethylformamide / 10 h / 40 °C

5: 95 percent / Ph₃P / CH₂Cl₂ / 0.5 h / 20 °C

6: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

With sodium hydroxide; sodium periodate; dipyridinium dichromate; n-butyllithium; sodium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Oxidation / 2: Condensation / 3: Alkylation / 4: Oxidation / 5: Condensation / 6: Dehydrobromination;
DOI:10.1271/bbb.63.736

Reference yield:

: 69940-02-9,142226-15-1,115693-78-2
3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

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

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / AcOH / H₂O / 21 h / 20 °C

2: NaIO₄ / H₂O / 1.5 h / 20 °C

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

4: 66 percent / NaH / dimethylformamide / 6 h / -20 °C

5: 76 percent / pyridinium dichromate / dimethylformamide / 10 h / 40 °C

6: 95 percent / Ph₃P / CH₂Cl₂ / 0.5 h / 20 °C

7: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

With sodium hydroxide; sodium periodate; dipyridinium dichromate; n-butyllithium; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Oxidation / 3: Condensation / 4: Alkylation / 5: Oxidation / 6: Condensation / 7: Dehydrobromination;
DOI:10.1271/bbb.63.736