Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

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Chemical Name:Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate
CAS No.:122490-56-6
Molecular Formula:C₃₇H₄₈O₇Si
Molecular Weight:632.869
Hs Code.:

Synonyms:Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

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Chemical Property of Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

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Technology Process of Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

There total 12 articles about Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate 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: 89.0%

: 122490-55-5
3,7-Anhydro-10-O-(tert-butyldiphenylsilyl)-2,5,8,9-tetradeoxy-6-O-(p-methoxybenzyl)-L-allo-deconal

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 122490-56-6
Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

Guidance literature:: In benzene; at 25 ℃; for 1h;
DOI:10.1021/ja00199a029

Reference yield:

: 82740-87-2
(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate

: 122490-56-6
Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / K₂CO₃ / methanol / 4 h / 25 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 3 h

3: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 1 h, 2.) 15 min

4: 45 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h

5: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6: 1.) BF₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 15 min

7: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 3 h

8: 86 percent / amberlyst-15 (H+) / methanol / 0.75 h / 25 °C

9: 85 percent / pyridine / 4 h / 0 °C

10: 91 percent / dimethylsulfoxide / 2 h / 70 °C

11: DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

12: 89 percent / benzene / 1 h / 25 °C

With pyridine; 1H-imidazole; sodium hydroxide; borane-THF; 2-methyl-but-2-ene; boron trifluoride-tetrahydrofuran complex; Amberlyst-15 (H+); hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; palladium dihydroxide; In methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00199a029

Reference yield:

: 95791-07-4
(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

: 122490-56-6
Methyl (E)-(2R,3S,5R,6S)-6-<3-(tert-butyldiphenylsiloxy)propyl>tetrahydro-3-hydroxy-5-<(p-methoxybenzyl)oxy>-2H-pyran-2-crotonate

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 3 h

2: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 1 h, 2.) 15 min

3: 45 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h

4: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

5: 1.) BF₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 15 min

6: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 3 h

7: 86 percent / amberlyst-15 (H+) / methanol / 0.75 h / 25 °C

8: 85 percent / pyridine / 4 h / 0 °C

9: 91 percent / dimethylsulfoxide / 2 h / 70 °C

10: DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

11: 89 percent / benzene / 1 h / 25 °C

With pyridine; 1H-imidazole; sodium hydroxide; borane-THF; 2-methyl-but-2-ene; boron trifluoride-tetrahydrofuran complex; Amberlyst-15 (H+); hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; palladium dihydroxide; In methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00199a029