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
• Mol file: 851387-20-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

p-toluenesulfonyl chloride (98-59-9) + 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-α-D-lyxo-furanoside (851387-19-4) → 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside (851387-20-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1016/j.tetasy.2005.01.046

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (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) → 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside (851387-20-7)

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:

1-but-3-ynyloxymethyl-4-methoxy-benzene (218434-90-3) → 4-(4-methoxybenzyloxy)butyn-1-yl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxo-furanoside (851387-20-7)

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

upstream raw materials:

p-toluenesulfonyl chloride

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

2,3,5,6-di-O-isopropylidene-D-mannofuranose

1-but-3-ynyloxymethyl-4-methoxy-benzene

Downstream raw materials:

4-(N,O-bis(phenoxycarbonyl)hydroxylamino)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

4-(N-hydroxylureidyl)butyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

4-hydroxybutyn-1-yl 2,3-O-isopropylidene-5-O-(4-fluorophenyl)-α-D-lyxo-furanoside

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