(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

Base Information

Chemical Name:(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol
CAS No.:848737-88-2
Molecular Formula:C₂₂H₄₀O₄Si
Molecular Weight:396.643
Hs Code.:

Synonyms:(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

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Chemical Property of (2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

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Technology Process of (2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

There total 9 articles about (2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol 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: 70.0%

: 848737-86-0
(2R,3R,4S,6R)-7-(t-butyldimethylsilyloxy)-2,3-benzylidendioxy-4,6-dimethyl-1-heptanol

: 848737-88-2
(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

Guidance literature:: (2R,3R,4S,6R)-7-(t-butyldimethylsilyloxy)-2,3-benzylidendioxy-4,6-dimethyl-1-heptanol; With dimethylsulfide borane complex; In dichloromethane; at 0 - 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tet.2004.12.013

Reference yield:

: 848737-82-6
ethyl (2E,4S,6R)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6-dimethyl-2-heptenoate

: 848737-88-2
(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 45 h / 20 °C

2.1: 83 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1 h / 20 °C

3.1: 83 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C

4.1: borane-dimethylsulfide complex / CH₂Cl₂ / 1 h / 0 - 20 °C

4.2: 70 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

With lithium aluminium tetrahydride; methanesulfonamide; dimethylsulfide borane complex; AD-mix-β; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/j.tet.2004.12.013

Reference yield:

: 848737-84-8
(2S,3R,4S,6R)-ethyl 7-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4,6-dimethylheptanoate

: 848737-88-2
(2R,3R,4S,6R)-3-benzyloxy-7-(t-butyldimethylsilyloxy)-4,6-dimethyl-1,2-heptanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1 h / 20 °C

2.1: 83 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h / 0 °C

3.1: borane-dimethylsulfide complex / CH₂Cl₂ / 1 h / 0 - 20 °C

3.2: 70 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

With lithium aluminium tetrahydride; dimethylsulfide borane complex; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2004.12.013