(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

Base Information

Chemical Name:(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol
CAS No.:263405-38-5
Molecular Formula:C₂₇H₃₈ClNO₇SeSi
Molecular Weight:631.1
Hs Code.:

(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

Synonyms:(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

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Chemical Property of (+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

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Technology Process of (+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

There total 7 articles about (+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol 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: 75.0%

: 263405-37-4
(-)-(1S,3R,4R,5R,6R)-6-endo-chloro-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one

: 263405-38-5
(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at 5 ℃;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

: 223421-32-7
(+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde

: 263405-38-5
(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

2: aq. HCl / 0 °C

3: 70 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

4: 75 percent / NaBH₄ / methanol; CH₂Cl₂ / 5 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 1: Addition / 2: Isomerization / 3: silylation / 4: Reduction;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 263405-38-5
(+)-(1S,2R,3S,4R,5R,6R)-3-endo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aR,4aR,7aR,7bS)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-endo-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 75 percent / NaBH₄ / methanol; CH₂Cl₂ / 5 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; In methanol; dichloromethane; 1: silylation / 2: Reduction;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I