5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS No.: 495406-24-1
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 495406-24-1.mol

Synonyms:5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property of 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

There total 3 articles about 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol 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: 77.0%

5-tert-butyldimethylsilyloxymethyl-6-[4-(4-methoxybenzyloxy)-1-butynyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (495406-23-0) → 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (495406-24-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0957-4166(02)00466-4

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (495406-24-1)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 50 percent / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

2.1: 77 percent / LiAlH₄ / tetrahydrofuran / 12 h / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0957-4166(02)00466-4

Reference yield:

1-but-3-ynyloxymethyl-4-methoxy-benzene (218434-90-3) → 5-hydroxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol (495406-24-1)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 50 percent / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

2.1: 77 percent / LiAlH₄ / tetrahydrofuran / 12 h / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0957-4166(02)00466-4

upstream raw materials:

5-tert-butyldimethylsilyloxymethyl-6-[4-(4-methoxybenzyloxy)-1-butynyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

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

Downstream raw materials:

5-tert-butyldimethylsilyloxymethyl-6-[4-(4-methoxybenzyloxy)-(E)-1-butenyl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-ol

1-[6-hydroxy-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl]-4-(4-methoxybenzyloxy)-2-methylcarbonyloxy-(1R,2S)-butyl acetate

1-[6-hydroxy-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl]-4-(4-methoxybenzyloxy)-(1S,2R)-butane-1,2-diol

1-[6-hydroxy-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl]-4-(4-methoxybenzyloxy)-(1R,2S)-butane-1,2-diol