(-)-(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

Base Information

Chemical Name:(-)-(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
CAS No.:263405-37-4
Molecular Formula:C₂₇H₃₆ClNO₇SeSi
Molecular Weight:629.084
Hs Code.:

(-)-(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

Synonyms:(-)-(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

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Chemical Property of (-)-(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

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Technology Process of (-)-(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

There total 5 articles about (-)-(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 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: 70.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 263405-36-3
(1S,3R,4R,5R,6R)-6-endo-chloro-3-endo-{(S)-hydroxy[(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

: 263405-37-4
(-)-(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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 6h;
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

: 263405-37-4
(-)-(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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 128573-16-0
(-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one

: 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

Guidance literature:: Multi-step reaction with 3 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

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