(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

Base Information

Chemical Name:(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene
CAS No.:115435-01-3
Molecular Formula:C₂₉H₃₄O₃Si
Molecular Weight:458.673
Hs Code.:

Synonyms:(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

Chemical Property:

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Technology Process of (3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

There total 9 articles about (3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene 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: 10.0%

: 115435-03-5
(S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-3-enone

: 115435-01-3
(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

: 115509-81-4
(3S,4R)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
DOI:10.1246/bcsj.60.3673

Reference yield:

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 115435-01-3
(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

Guidance literature:: Multi-step reaction with 9 steps

1: 80percent acetic acid / H₂O / Heating

2: 1.) conc. HCl / 1.) -15 min, 30 min; 2.) pyridine, r.t., 13 h

3: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

4: pyridine; acetic anhydride / 36 h / Ambient temperature

5: sodium borohydride / methanol / 0.5 h / -15 °C

7: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

8: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

9: 73 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; diisobutylaluminium hydride; acetic acid; calcium carbonate; sodium chloride; mercury dichloride; In pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1246/bcsj.60.3673

Reference yield:

: 3-O-Benzyl-D-xylose

: 115435-01-3
(3S,4S)-3-(benzyloxy)-1-<<(t-butyldiphenylsilyl)oxy>methyl>-4-hydroxy-1-cyclopentene

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) conc. HCl / 1.) -15 min, 30 min; 2.) pyridine, r.t., 13 h

2: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

3: pyridine; acetic anhydride / 36 h / Ambient temperature

4: sodium borohydride / methanol / 0.5 h / -15 °C

6: NaCl / dimethylsulfoxide; H₂O / 110 - 160 deg C, 2 h; 160 deg C, 4 h

7: 75 percent / DIBAL-H / CH₂Cl₂; toluene / -78 °C

8: 73 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; diisobutylaluminium hydride; calcium carbonate; sodium chloride; mercury dichloride; In pyridine; methanol; dichloromethane; water; acetic anhydride; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1246/bcsj.60.3673