(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

Base Information

Chemical Name:(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol
CAS No.:113656-57-8
Molecular Formula:C₃₆H₅₈O₇Si
Molecular Weight:630.938
Hs Code.:

Synonyms:(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

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Chemical Property of (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

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Technology Process of (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

There total 21 articles about (2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol 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: 100.0%

: 120269-74-1
(2R,3R,6S)-6-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxy)-heptane-1,3,6-triol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 113656-57-8
(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

Guidance literature:: With 1H-imidazole; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.37.1705

Reference yield:

: 113643-40-6
<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran>-2-methanol

: 113656-57-8
(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1: CrO₃, H₂SO₄ / acetone / 0 °C

3: n-BuLi / tetrahydrofuran / -93 °C

4: 1.) NaH; 2.) H₂ / 2.) Pd-C / 1.) DMSO-THF, 0 deg C; 2.) AcOEt

5: 87 percent / diethyl ether / -93 °C

6: 96 percent / 1N-HCl / tetrahydrofuran / Ambient temperature

7: 95 percent / imidazole / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; chromium(VI) oxide; hydrogenchloride; n-butyllithium; sulfuric acid; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)95485-6

Reference yield:

: (2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-carboxylic acid

: 113656-57-8
(2S,5R,6R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-7-tert-butyldimethylsilyloxy-6-(4-methoxybenzyloxy)heptane-2,5-diol

Guidance literature:: Multi-step reaction with 6 steps

2: n-BuLi / tetrahydrofuran / -93 °C

3: 1.) NaH; 2.) H₂ / 2.) Pd-C / 1.) DMSO-THF, 0 deg C; 2.) AcOEt

4: 87 percent / diethyl ether / -93 °C

5: 96 percent / 1N-HCl / tetrahydrofuran / Ambient temperature

6: 95 percent / imidazole / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; hydrogenchloride; n-butyllithium; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)95485-6