Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

Base Information

Chemical Name:Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)
CAS No.:130335-92-1
Molecular Formula:C₂₀H₃₆O₃Si
Molecular Weight:352.59
Hs Code.:

Synonyms:Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

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Chemical Property of Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

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Technology Process of Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

There total 6 articles about Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5) 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:

: 134948-79-1
Ethyl 4-O-(tert-butyldimethylsilyl)-2,3-dideoxy-6-O-pivaloyl-α-D-erythro-hex-2-enopyranoside

: 130335-92-1
Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 5 °C

2: 57 percent / 1,3-dicyclohexylcarbodiimide, dimethyl sulfoxide, H₃PO₄ / 16 h / Ambient temperature

3: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h

With lithium aluminium tetrahydride; phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)87085-X

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 130335-92-1
Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / DMAP / CH₂Cl₂ / 3 h / Heating

2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 5 °C

3: 57 percent / 1,3-dicyclohexylcarbodiimide, dimethyl sulfoxide, H₃PO₄ / 16 h / Ambient temperature

4: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h

With dmap; lithium aluminium tetrahydride; phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)87085-X

Reference yield:

: 3323-72-6
ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

: 130335-92-1
Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5)

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / DMAP / CH₂Cl₂ / 3 h / Heating

2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 5 °C

3: 57 percent / 1,3-dicyclohexylcarbodiimide, dimethyl sulfoxide, H₃PO₄ / 16 h / Ambient temperature

4: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h

With dmap; lithium aluminium tetrahydride; phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)87085-X