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

Base Information

Chemical Name: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
CAS No.:495406-29-6
Molecular Formula:C₃₀H₄₈O₁₁Si
Molecular Weight:612.79
Hs Code.:

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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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:

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 495406-29-6
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

Guidance literature:: Multi-step reaction with 5 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

3.1: 80 percent / imidazole / CH₂Cl₂ / 12 h

4.1: 70 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

5.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

With 1H-imidazole; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0957-4166(02)00466-4

Reference yield:

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

: 495406-29-6
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

Guidance literature:: Multi-step reaction with 5 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

3.1: 80 percent / imidazole / CH₂Cl₂ / 12 h

4.1: 70 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

5.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

With 1H-imidazole; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetone;
DOI:10.1016/S0957-4166(02)00466-4

Reference yield:

: 495406-24-1
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

: 495406-29-6
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

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / imidazole / CH₂Cl₂ / 12 h

2: 70 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

3: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

With 1H-imidazole; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone;
DOI:10.1016/S0957-4166(02)00466-4