dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

Base Information

Chemical Name:dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane
CAS No.:112918-34-0
Molecular Formula:C₂₉H₃₁N₃O
Molecular Weight:437.585
Hs Code.:

Synonyms:dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

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Chemical Property of dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

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Technology Process of dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

There total 6 articles about dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<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:

: Methanesulfonic acid (1S,2S,3R,5S)-6,6-dimethyl-2-(2-trityloxy-ethyl)-bicyclo[3.1.0]hex-3-yl ester

: 112918-34-0
dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; for 5h;
DOI:10.1021/jm00163a038

Reference yield:

: 112918-30-6
dl-(1α,2α,3α,5α)-3-acetoxy-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 112918-34-0
dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 2 N aq. NaOH / methanol; tetrahydrofuran / 3 h / Heating

2: 99 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -60 °C

3: 75 percent / t-BuOK / dimethylformamide / 8 h / Ambient temperature

4: 60 percent / lithium tri-tert-butoxyaluminiumhydride / tetrahydrofuran / 2.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: NaN₃ / dimethylformamide / 5 h / 75 °C

With sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038

Reference yield:

: 112945-29-6
dl-(1β,2α,3α,5β)-6,6-dimethyl-3-hydroxy-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 112918-34-0
dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: NaN₃ / dimethylformamide / 5 h / 75 °C

With sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038