[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

Base Information

Chemical Name:[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol
CAS No.:261968-19-8
Molecular Formula:C₂₃H₄₂O₅Si
Molecular Weight:426.669
Hs Code.:

Synonyms:[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

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Chemical Property of [2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

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Technology Process of [2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

There total 12 articles about [2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-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: 86.0%

: Benzoic acid (1S,3S,4R,5S)-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5-trimethyl-hexyl ester

: 261968-19-8
[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 20h;
DOI:10.1021/ja011211m

Reference yield: 85.0%

: 261968-18-7
(2S,4R,5R,6S)-2-benzoyloxy-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-3-one

: 261968-19-8
[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -27 ℃; for 3h;
DOI:10.1002/(SICI)1521-3773(20000117)39:2<377::AID-ANIE377>3.0.CO;2-E

Reference yield:

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: 261968-19-8
[2S,4S,5R,6S]-7-(t-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-4,6-dimethylheptan-2,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Me₂NEt / diethyl ether / 1.5 h / 0 °C

2.1: diethyl ether / 19 h / -78 - -20 °C

2.2: 99 percent / 30 percent aq. hydrogen peroxide / methanol / 0 - 20 °C / pH 7

3.1: 93 percent / triflic acid / diethyl ether / 10 h / 20 °C

4.1: NaBH₄ / methanol; H₂O / 0 - 20 °C

5.1: 86 percent / K₂CO₃ / methanol / 20 h / 20 °C

With sodium tetrahydroborate; N,N-dimethyl-ethanamine; trifluorormethanesulfonic acid; potassium carbonate; In methanol; diethyl ether; water;
DOI:10.1021/ja011211m