(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

Base Information

Chemical Name:(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime
CAS No.:244612-17-7
Molecular Formula:C₄₃H₄₉NO₅Si
Molecular Weight:687.951
Hs Code.:

Synonyms:(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

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Chemical Property of (Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

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Technology Process of (Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

There total 10 articles about (Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime 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: 83.0%

: 103587-51-5
O-(tert-butyl)diphenylsilylhydroxylamine

: 2,3,4-tri-O-benzyl-6-deoxy-D-altropyranose

: 244612-17-7
(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

: 244612-16-6
(E)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

Guidance literature:: With 3 A molecular sieve; pyridinium p-toluenesulfonate; In dichloromethane; at 22 ℃; for 72h;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3

Reference yield:

: 93382-48-0
allyl 4,6-O-benzylidene-α-D-glucopyranoside

: 244612-17-7
(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / pyridine / 6 h / 21 °C

2: 82 percent / Na / 15.5 h / 21 - 90 °C

3: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 60 °C

4: 75 percent / LiAlH₄; Me₃SiBr / diethyl ether / 0.5 h / Heating

5: 75 percent / pyridine / 4 h / 22 °C

6: 92 percent / LiAlH₄ / diethyl ether / 2 h / Heating

7: {Ir(cod)[PMePh₂]2}PF₆-H₂ / tetrahydrofuran / 21 °C

8: HgO; HgCl₂ / acetone; H₂O / 0.25 h / 21 °C

9: 13 percent / pyridinium p-toluenesulfonate; molecular sieves 3 Angstroem / CH₂Cl₂ / 72 h / 22 °C

With lithium aluminium tetrahydride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl bromide; 3 A molecular sieve; hydrogen; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; acetone; 1: Esterification / 2: Substitution / 3: Aralkylation / 4: Reduction / 5: Acylation / 6: Reduction / 7: Isomerization / 8: Hydrolysis / 9: Condensation;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3

Reference yield:

: 100-39-0
benzyl bromide

: 244612-17-7
(Z)-2,3,4-tri-O-benzyl-6-deoxy-D-altrose O-[(tert-butyl)diphenylsilyl]oxime

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 60 °C

2: 75 percent / LiAlH₄; Me₃SiBr / diethyl ether / 0.5 h / Heating

3: 75 percent / pyridine / 4 h / 22 °C

4: 92 percent / LiAlH₄ / diethyl ether / 2 h / Heating

5: {Ir(cod)[PMePh₂]2}PF₆-H₂ / tetrahydrofuran / 21 °C

6: HgO; HgCl₂ / acetone; H₂O / 0.25 h / 21 °C

7: 13 percent / pyridinium p-toluenesulfonate; molecular sieves 3 Angstroem / CH₂Cl₂ / 72 h / 22 °C

With lithium aluminium tetrahydride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl bromide; 3 A molecular sieve; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; acetone; 1: Aralkylation / 2: Reduction / 3: Acylation / 4: Reduction / 5: Isomerization / 6: Hydrolysis / 7: Condensation;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<1044::AID-HLCA1044>3.0.CO;2-3