(-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep...

Base Information

• Chemical Name: (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep...
• CAS No.: 263405-44-3
• Molecular Formula: C₂₉H₄₂ClNO₈SeSi
• Molecular Weight: 675.153

Synonyms:(-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep...

Chemical Property of (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep...

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep...

There total 4 articles about (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep... 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: 97.0%

chloromethyl methyl ether (107-30-2) + (-)-(1S,2R,3S,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-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 (263405-31-8) → (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep... (263405-44-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 25 ℃; for 21h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep... (263405-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

1.3: 41 percent / NaBH₄ / methanol / 0 °C

2.1: 97 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; 1.1: Addition / 1.2: silylation / 1.3: Reduction / 2.1: Substitution;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

(-)-(1S,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one (128573-16-0) → (-)-(1S,2R,3R,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-endo-chloro-2-endo-(methoxymethoxy)-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]hep... (263405-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

1.3: 41 percent / NaBH₄ / methanol / 0 °C

2.1: 97 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; 1.1: Addition / 1.2: silylation / 1.3: Reduction / 2.1: Substitution;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

upstream raw materials:

chloromethyl methyl ether

(-)-(1S,2R,3S,4R,5R,6R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(-)-(1R,2R,4S,5R,6R)-6-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aS,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-5-endo-(methoxymethoxy)-3-oxo-7-oxabicyclo[2.2.1]hept-2-exo-yl 4-bromobenzenesulfonate

1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

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