ChemicalBook CAS DataBase List 4H-1,3-Dioxolo[4,5-c]pyrrole, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5-(phenylmethyl)-, (3aR,4R,6aS)-

4H-1,3-Dioxolo[4,5-c]pyrrole, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5-(phenylmethyl)-, (3aR,4R,6aS)- synthesis

6synthesis methods

Product Name:4H-1,3-Dioxolo[4,5-c]pyrrole, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5-(phenylmethyl)-, (3aR,4R,6aS)-
CAS Number:153172-30-6
Molecular formula:C21H35NO3Si
Molecular Weight:377.59

18162-48-6 Synthesis

18162-48-6
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[(3aR,4R,6aS)-5-benzyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methanol

117858-84-1
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4H-1,3-Dioxolo[4,5-c]pyrrole, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-5-(phenylmethyl)-, (3aR,4R,6aS)-

153172-30-6
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Yield:153172-30-6 98%

Reaction Conditions:

with 1H-imidazole;dmap in dichloromethane at 20; for 10 h;Inert atmosphere;

Steps:

4.1. 1-Amino-1,4-anhydro-N-benzyl-5-O-tert-butyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-d-ribitol (7)

To a stirred solution of 6refPreviewPlaceHolder³⁷ (150 mg, 0.57 mmol) in anhydrous CH₂Cl₂ (5 mL) at rt under Ar atmosphere were added DMAP (7 mg, 0.05 mmol) and imidazole (93 mg, 1.36 mmol) followed by TBDMSCl (103 mg, 0.68 mmol). The mixture was then stirred for 10 h and partitioned (CH₂Cl₂//·NaHCO₃/H₂O). The organic layer was washed (brine), dried (MgSO₄) and evaporated. The residue was purified by column chromatography (15% EtOAc/hexane) to give 7refPreviewPlaceHolder⁵⁰ (204 mg, 98%) as a colorless oil. ¹H NMR δ -0.13 (s, 3, CH₃), 0.00 (s, 3, CH₃), 0.83 (s, 9, t-Bu), 1.26 (s, 3, CH₃), 1.49 (s, 3, CH₃), 2.65 (dd, J = 2.7, 10.3 Hz, 1, H1), 2.94 (‘q’, J = , 2.2 Hz, 1, H4), 3.04 (dd, J = 5.5, 10.3 Hz, 1, H1'), 3.57 (dd, J = 4.1, 10.6 Hz, 1, H5), 3.64 (d, J = 13.4 Hz, 1, Bn), 3.71 (dd, J = 4.3, 10.6 Hz, 1, H5'), 3.94 (d, J = 13.4 Hz, 1, Bn), 4.49 (dd, J = 2.0, 6.5 Hz, 1, H3), 4.58 (‘dt’, J = 2.7, 6.2 Hz, 1, H2), 7.13-7.23 (m, 5, Bn); ¹³C NMR δ -5.5, (CH₃), -5.4, (CH₃), 18.2 (t-Bu), 25.2 (CMe₂), 25.7 (CH₃), 25.9 (CH₃), 27.2 (CMe₂), 56.9 (Bn), 59.3 (C1), 63.2 (C5), 68.9 (C4), 79.4 (C2), 83.3 (C3), 111.9 (CMe₂), 128.2, 128.5, 126.8, 139.4 (Bn); MS (APCI) m/z 378 (100, MH⁺).

References:

Malladi, Venkata L.A.;Sobczak, Adam J.;Meyer, Tiffany M.;Pei, Dehua;Wnuk, Stanislaw F. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 18,p. 5507 - 5519] Location in patent:experimental part

D-Ribonic acid, 2,3-O-(1-methylethylidene)-, γ-lactone, 5-methanesulfonate

89747-54-6
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153172-30-6
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References

2,3-O-ISOPROPYLIDENE-L-LYXONO-1,4-LACTONE

152006-17-2
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153172-30-6
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References

1044813-00-4 Synthesis

5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone

1044813-00-4
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153172-30-6
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References

5336-08-3
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153172-30-6
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