(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

Base Information

Chemical Name:(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane
CAS No.:124871-59-6
Molecular Formula:C₂₈H₄₂O₄Si
Molecular Weight:470.725
Hs Code.:

Synonyms:(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

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Technology Process of (2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

There total 6 articles about (2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane 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: 89.0%

: 917-64-6
methyl magnesium iodide

: 114825-89-7
(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal

: 124871-59-6
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

Guidance literature:: In diethyl ether; at -15 ℃; for 1h;
DOI:10.1248/cpb.37.1167

Reference yield:

: 97058-14-5
(2R,3S,4R)-3,5-(Isopropylidenedioxy)-2,4-dimethylpentanal

: 124871-59-6
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 1.5M n-BuLi / hexane; tetrahydrofuran / -50 deg C, -23/-20 deg C, 2.5 h, -80 deg C, 40 min

2: 92 percent / 4N HCl / tetrahydrofuran / 11 h / Ambient temperature

3: 93 percent / imidazole / CH₂Cl₂ / 2 h / Ambient temperature

4: 79 percent / PPTS / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 88 percent / MeI, NaHCO₃ / acetonitrile / 1.5 h / 70 °C

6: 89 percent / diethyl ether / 1 h / -15 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1248/cpb.37.1167

Reference yield:

: 114825-88-6
(2R,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-3,5-dimethyl-2,4-isopropylidenedioxyhexanal trimethylene dithioacetal

: 124871-59-6
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / MeI, NaHCO₃ / acetonitrile / 1.5 h / 70 °C

2: 89 percent / diethyl ether / 1 h / -15 °C

With sodium hydrogencarbonate; methyl iodide; In diethyl ether; acetonitrile;
DOI:10.1248/cpb.37.1167