(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

Base Information

Chemical Name:(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one
CAS No.:102717-45-3
Molecular Formula:C₂₃H₃₀O₅Si
Molecular Weight:414.574
Hs Code.:

Synonyms:(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

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Chemical Property of (3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

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Technology Process of (3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

There total 8 articles about (3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one 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:

: 102916-19-8
(S)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-dihydro-furan-2-one

: 102744-94-5
(3S,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

: 102717-45-3
(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

Guidance literature:: With MoO₅*pyridine*HMPA; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(01)80905-9

Reference yield:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 102717-45-3
(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) LiN(TMS)2; 2.) MoOPH / 1.) THF, -78 deg C, 30 min; 2.) 1 h

2: 76 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 deg C to room temp.

3: 82 percent / CSA / 4 h

4: 1.) MsCl ; 2.) Bu₄N⁽¹⁺⁾*F^(1-) / 1.) pyridine , DMAP , 12 h ; 2.) THF , room temp., 1 h

5: 1.) LiN(TMS)2 / 1.) THF , 0 deg C to room temp.; 2.) 18 h

6: ethyl(dimethylaminoethyl)carbidiimide HCl, DMAP / diethyl ether

8: LiN(TMS)2 , MoOPh / tetrahydrofuran / -78 °C

With dmap; sodium tetrahydroborate; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methanesulfonyl chloride; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; water;
DOI:10.1016/S0040-4039(01)80905-9

Reference yield:

: 102717-43-1
(R)-5-((R)-2,2-Diethyl-[1,3]dioxolan-4-ylmethyl)-3-phenylsulfanyl-dihydro-furan-2-one

: 102717-45-3
(3R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-3-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

2: LiN(TMS)2 , MoOPh / tetrahydrofuran / -78 °C

With MoO₅*pyridine*HMPA; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1016/S0040-4039(01)80905-9