3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

Base Information

Chemical Name:3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose
CAS No.:143135-33-5
Molecular Formula:C₃₀H₄₀O₆Si
Molecular Weight:524.73
Hs Code.:

Synonyms:3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

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Chemical Property of 3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

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Technology Process of 3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

There total 8 articles about 3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose 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:

: 143135-40-4,143135-41-5,143135-43-7,143135-44-8
5-(tert-Butyl-diphenyl-silanyloxy)-1-[(3aR,5S,6R,6aR)-5-(1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentan-2-ol

: 143135-33-5
3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 4h;
DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

: 18427-19-5
1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

: 143135-33-5
3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

Guidance literature:: Multi-step reaction with 8 steps

1: PCC, molecular sieves 4A / CH₂Cl₂ / 0.75 h

2: 87 percent / tetrahydrofuran / 0.75 h / Ambient temperature

3: 1) BH₃*THF, 2) 35percent aq. H₂O₂, 3M aq. NaOH / 1) THF, 0 deg C, 3h, 2) water, 30 min

4: imidazole / dimethylformamide / 3 h

5: 64 percent / AcOH / tetrahydrofuran; H₂O / 15 h

6: 681 mg / NaIO₄ / methanol; H₂O / 1 h

7: 731 mg / tetrahydrofuran / 0.5 h / Heating

8: 558 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

With 1H-imidazole; sodium hydroxide; sodium periodate; borane-THF; 4 A molecular sieve; dihydrogen peroxide; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80440-3

Reference yield:

: 143135-48-2,143135-49-3
5-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-pentane-1,4-diol

: 143135-33-5
3,6-Dideoxy-1,2-O-isopropylidene-3-C-<2-oxo-5-<(tert-butyldiphenylsilyl)oxy>pentyl>-α-D-allofuran-5-ulose

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 3 h

2: 64 percent / AcOH / tetrahydrofuran; H₂O / 15 h

3: 681 mg / NaIO₄ / methanol; H₂O / 1 h

4: 731 mg / tetrahydrofuran / 0.5 h / Heating

5: 558 mg / PCC, molecular sieves 4A / CH₂Cl₂ / 4 h

With 1H-imidazole; sodium periodate; 4 A molecular sieve; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80440-3