(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

Base Information

Chemical Name:(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane
CAS No.:146514-65-0
Molecular Formula:C₃₄H₄₅N₃O₄Si
Molecular Weight:587.835
Hs Code.:

Synonyms:(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

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Chemical Property of (1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

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Technology Process of (1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

There total 13 articles about (1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane 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:

: 85716-45-6
1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon

: 146514-65-0
(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

Guidance literature:: Multi-step reaction with 9 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

2: LDA / tetrahydrofuran; hexane / -70 °C

3: Et₂Zn / toluene / 0 deg C, 1 h, to r.t., 2 h

4: FeCl₃ / dimethylformamide / 2 h / 70 °C

5: NaOAc / methanol / 1.5 h / Heating

6: 90 percent / H₂ / 10percent Pd/C / ethanol

7: 50 percent / NaBH₄ / dioxane / Ambient temperature

8: DMAP, pyridine / Ambient temperature

9: NaN₃ / dimethylformamide / 90 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium azide; hydrogen; diethylzinc; sodium acetate; iron(III) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89584-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 146514-65-0
(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

Guidance literature:: Multi-step reaction with 9 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

2: LDA / tetrahydrofuran; hexane / -70 °C

3: Et₂Zn / toluene / 0 deg C, 1 h, to r.t., 2 h

4: FeCl₃ / dimethylformamide / 2 h / 70 °C

5: NaOAc / methanol / 1.5 h / Heating

6: 90 percent / H₂ / 10percent Pd/C / ethanol

7: 50 percent / NaBH₄ / dioxane / Ambient temperature

8: DMAP, pyridine / Ambient temperature

9: NaN₃ / dimethylformamide / 90 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium azide; hydrogen; diethylzinc; sodium acetate; iron(III) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89584-3

Reference yield:

: 100-39-0
benzyl bromide

: 146514-65-0
(1S,2R,3S,4R,5S) 1-azido-5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cycloheptane

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH; 2.) n-Bu₄NI / 1.) THF, r.t., 1 h, 60 deg C, 1 h; 2.) THF, r.t., 1 h, 40 deg C, 1 h

2: 72 percent / Hg(OAc)2 / acetone; acetic acid; H₂O / 5 h / Heating

3: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

4: LDA / tetrahydrofuran; hexane / -70 °C

5: Et₂Zn / toluene / 0 deg C, 1 h, to r.t., 2 h

6: FeCl₃ / dimethylformamide / 2 h / 70 °C

7: NaOAc / methanol / 1.5 h / Heating

8: 90 percent / H₂ / 10percent Pd/C / ethanol

9: 50 percent / NaBH₄ / dioxane / Ambient temperature

10: DMAP, pyridine / Ambient temperature

11: NaN₃ / dimethylformamide / 90 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium azide; mercury(II) diacetate; hydrogen; diethylzinc; sodium acetate; iron(III) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(01)89584-3