1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Base Information

Chemical Name:1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone
CAS No.:797035-79-1
Molecular Formula:C₃₅H₄₆O₅Si
Molecular Weight:574.833
Hs Code.:

Synonyms:1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

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Chemical Property of 1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

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Technology Process of 1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

There total 18 articles about 1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone 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: 91.0%

: 852143-72-7
1-[(2S,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

: 797035-79-1
1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Guidance literature:: With potassium hexamethylsilazane; lithium chloride; In toluene; at 55 ℃; for 2h;
DOI:10.1021/jo050034v

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 797035-79-1
1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Guidance literature:: Multi-step reaction with 8 steps

1: 79.3 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 81 percent / dimethylsulfoxide / 12 h / 75 °C

3: DIBAL / toluene; CH₂Cl₂ / 1 h / -78 °C

4: 181 mg / NaBH₄ / methanol / 0.5 h / 0 °C

5: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

6: HIO₄ / ethyl acetate / 6 h / 0 °C

7: tetrahydrofuran; diethyl ether / 1 h / -78 °C

8: 49 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; Dess-Martin periodane; periodic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 8: Dess-Martin oxidation;
DOI:10.1002/chem.200500892

Reference yield:

: 797035-75-7
[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

: 797035-79-1
1-[(2R,3R,4S,5S,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: DIBAL / toluene; CH₂Cl₂ / 1 h / -78 °C

2: 181 mg / NaBH₄ / methanol / 0.5 h / 0 °C

3: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

4: HIO₄ / ethyl acetate / 6 h / 0 °C

5: tetrahydrofuran; diethyl ether / 1 h / -78 °C

6: 49 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; diisobutylaluminium hydride; Dess-Martin periodane; periodic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene; 6: Dess-Martin oxidation;
DOI:10.1002/chem.200500892