ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

Base Information

Chemical Name:ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate
CAS No.:869348-61-8
Molecular Formula:C₂₄H₄₂O₆Si
Molecular Weight:454.679
Hs Code.:

Synonyms:ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

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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 ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

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Technology Process of ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

There total 4 articles about ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate 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: 85.0%

: 869348-60-7
ethyl (R,E)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2-methyl-2-octenoate

: 869348-61-8
ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

Guidance literature:: With potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 - 20 ℃;
DOI:10.1021/ol051507n

Reference yield:

: 869348-19-6
(R)-1-benzyloxy-6-hepten-3-ol

: 869348-61-8
ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / imidazole; TBAI / dimethylformamide / 1 h

2: 88 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 5 h / Heating

3: 85 percent / AD-mix β; methanesulfonamide; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; tetra-(n-butyl)ammonium iodide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Sharpless dihydroxylation;
DOI:10.1021/ol051507n

Reference yield:

: 869348-59-4
ethyl (R,E)-7-benzyloxy-5-tert-butyldimethylsilyloxy-1-heptene

: 869348-61-8
ethyl (2S,3R,6R)-8-benzyloxy-6-tert-butyldimethylsilyloxy-2,3-dihydroxy-2-methyloctanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / Grubbs' second generation catalyst / CH₂Cl₂ / 5 h / Heating

2: 85 percent / AD-mix β; methanesulfonamide; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; tert-butyl alcohol; 2: Sharpless dihydroxylation;
DOI:10.1021/ol051507n