4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

Base Information

Chemical Name:4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside
CAS No.:851387-20-7
Molecular Formula:C₂₇H₃₂O₈S
Molecular Weight:516.612
Hs Code.:

Synonyms:4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

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Chemical Property of 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

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Technology Process of 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

There total 7 articles about 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside 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: 94.0%

: 98-59-9
p-toluenesulfonyl chloride

: 851387-19-4
4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-α-D-lyxo-furanoside

: 851387-20-7
4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 8h;
DOI:10.1016/j.tetasy.2005.01.046

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 851387-20-7
4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 43 percent / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: 93 percent / DEAD; PPh₃ / CH₂Cl₂ / 20 °C

3.1: 70 percent / HCl / methanol / 2 h / 20 °C

4.1: NaHCO₃; NaIO₄ / CH₂Cl₂ / 5 h / 20 °C

5.1: 60 percent / NaBH₄; MeOH / 0 - 20 °C

6.1: 94 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; sodium hydrogencarbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2005.01.046

Reference yield:

: 218434-90-3
1-but-3-ynyloxymethyl-4-methoxy-benzene

: 851387-20-7
4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 43 percent / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: 93 percent / DEAD; PPh₃ / CH₂Cl₂ / 20 °C

3.1: 70 percent / HCl / methanol / 2 h / 20 °C

4.1: NaHCO₃; NaIO₄ / CH₂Cl₂ / 5 h / 20 °C

5.1: 60 percent / NaBH₄; MeOH / 0 - 20 °C

6.1: 94 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; n-butyllithium; sodium hydrogencarbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2005.01.046