(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Base Information

Chemical Name:(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane
CAS No.:228394-01-2
Molecular Formula:C₂₂H₂₅N₃O₃
Molecular Weight:379.459
Hs Code.:

Synonyms:(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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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 (1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Technology Process of (1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

There total 11 articles about (1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane 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: 81.0%

: 199122-49-1
(1S,2S,3R,4S,5S)-1,2-di<(benzyloxy)methyl>-3,4-sulfinyldioxybicyclo<3.1.0>hexane

: 228394-01-2
(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 10h;
DOI:10.1021/jo990010m

Reference yield: 47.0%

: 228393-97-3
(1S,2S,3R,4S,5S)-1,2-di<(benzyloxy)methyl>-3,4-sulfonyldioxybicyclo<3.1.0>hexane

: 228394-01-2
(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
DOI:10.1021/jo990010m

Reference yield:

: 156126-13-5
(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

: 228394-01-2
(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 8 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

5: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

6: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

7: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

8: 81 percent / NaN₃ / dimethylformamide / 10 h / 100 °C

With hydrogenchloride; sodium perborate; n-butyllithium; thionyl chloride; sodium azide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo990010m