(S)-(3-benzyloxy-4-(2,3-epoxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Base Information

Chemical Name:(S)-(3-benzyloxy-4-(2,3-epoxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether
CAS No.:611179-93-2
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

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

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

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

There total 8 articles about (S)-(3-benzyloxy-4-(2,3-epoxy-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: 65.0%

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

: 611179-93-2
(S)-(3-benzyloxy-4-(2,3-epoxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: (R)-(3-benzyloxy-4-(2,3-dihydroxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether; With pyridine; methanesulfonyl chloride; In dichloromethane; at 20 ℃; for 12h;

With potassium carbonate; In methanol; for 4h; Heating;
DOI:10.1016/S0957-4166(03)00519-6

Reference yield:

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

: 611179-93-2
(S)-(3-benzyloxy-4-(2,3-epoxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 7 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

7.1: pyridine; MsCl / CH₂Cl₂ / 12 h / 20 °C

7.2: 65 percent / K₂CO₃ / methanol / 4 h / Heating

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; methanesulfonamide; AD-mix-β; sodium hydride; potassium carbonate; methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 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

: 611179-93-2
(S)-(3-benzyloxy-4-(2,3-epoxy-3-methylbutyl)-5-methoxymethoxybenzyl) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 6 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

6.1: pyridine; MsCl / CH₂Cl₂ / 12 h / 20 °C

6.2: 65 percent / K₂CO₃ / methanol / 4 h / Heating

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