(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Base Information

Chemical Name:(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether
CAS No.:611179-92-1
Molecular Formula:C₂₇H₄₂O₆Si
Molecular Weight:490.712
Hs Code.:

Synonyms:(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

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Chemical Property of (R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

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Technology Process of (R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

There total 7 articles about (R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether 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: 72.0%

: 611179-91-0
(3-benzyloxy-4-prenyl-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

: 611179-92-1
(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 0 ℃; for 36h;
DOI:10.1016/S0957-4166(03)00519-6

Reference yield:

: 2150-44-9
1-carbomethoxy-3,5-dihydroxybenzene

: 611179-92-1
(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 6 steps

1.1: 51 percent / K₂CO₃ / acetone / 3 h / Heating

2.1: 89 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: 91 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

4.1: 98 percent / imidazole / dimethylformamide / 1 h / 20 °C

5.1: BuLi; TMEDA / petroleum ether; tetrahydrofuran / 1 h / -20 - 0 °C

5.2: 70 percent / HMPA / petroleum ether; tetrahydrofuran / 2 h / -78 - 0 °C

6.1: 72 percent / AD-mix-β; NH2SO2CH3 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; methanesulfonamide; AD-mix-β; sodium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetone; Petroleum ether; tert-butyl alcohol; 6.1: Sharpless dihydroxylation;
DOI:10.1016/S0957-4166(03)00519-6

Reference yield:

: 54915-31-0
methyl 3-(benzyloxy)-5-hydroxybenzoate

: 611179-92-1
(R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: 91 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

3.1: 98 percent / imidazole / dimethylformamide / 1 h / 20 °C

4.1: BuLi; TMEDA / petroleum ether; tetrahydrofuran / 1 h / -20 - 0 °C

4.2: 70 percent / HMPA / petroleum ether; tetrahydrofuran / 2 h / -78 - 0 °C

5.1: 72 percent / AD-mix-β; NH2SO2CH3 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; methanesulfonamide; AD-mix-β; sodium hydride; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; Petroleum ether; tert-butyl alcohol; 5.1: Sharpless dihydroxylation;
DOI:10.1016/S0957-4166(03)00519-6