(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

Base Information

Chemical Name:(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one
CAS No.:855517-54-3
Molecular Formula:C₂₄H₃₇NO₅Si
Molecular Weight:447.647
Hs Code.:

Synonyms:(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

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Chemical Property of (1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

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Technology Process of (1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

There total 9 articles about (1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-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: 86.5%

: 855517-53-2
(1R,2R,3S,4S,5R)-1-O-mesyl-2-O-(benzylcarbamoyl)-3,4-O-isopropylidene-5-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-cyclopentane-1,2,3,4-tetrol

: 855517-54-3
(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 25 ℃; for 0.25h;
DOI:10.1039/b501824b

Reference yield:

: 261630-98-2
(1R,5R,8R)-8-Hydroxy-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 855517-54-3
(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / TfOH / dioxane / 0.17 h / 0 °C

2: OsO₄; NMO*H₂O / CH₂Cl₂ / 25 °C

3: 180 mg / H₂SO₄ / acetone / 0.5 h / 25 °C

4: 84 percent / LiAlH₄ / tetrahydrofuran / 0.08 h / 0 °C

5: 95 percent / DMAP / CH₂Cl₂ / 25 °C

6: 94 percent / pyridine; DMAP / CH₂Cl₂ / 25 °C

7: 79 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4.5 h / 25 °C

8: 98 percent / Et₃N / CH₂Cl₂ / 25 °C

9: 86.5 percent / t-BuOK / tetrahydrofuran / 0.25 h / 25 °C

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; sulfuric acid; potassium tert-butylate; hydrogen; 4-methylmorpholine N-oxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; acetone;
DOI:10.1039/b501824b

Reference yield:

: (3aR,6R,6aR)-6-Benzyloxy-4,5-dihydroxy-hexahydro-cyclopenta[b]furan-2-one

: 855517-54-3
(1S,2S,3S,4S,5S)-4-N-benzyl-6-(2-O-tert-butyldimethylsilyl-hydroxyethyl)-7,8-isopropylidenedioxy-2-oxa-4-azabicyclo[3.3.0]octan-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 180 mg / H₂SO₄ / acetone / 0.5 h / 25 °C

2: 84 percent / LiAlH₄ / tetrahydrofuran / 0.08 h / 0 °C

3: 95 percent / DMAP / CH₂Cl₂ / 25 °C

4: 94 percent / pyridine; DMAP / CH₂Cl₂ / 25 °C

5: 79 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4.5 h / 25 °C

6: 98 percent / Et₃N / CH₂Cl₂ / 25 °C

7: 86.5 percent / t-BuOK / tetrahydrofuran / 0.25 h / 25 °C

With pyridine; dmap; lithium aluminium tetrahydride; sulfuric acid; potassium tert-butylate; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone;
DOI:10.1039/b501824b