(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester
CAS No.:187227-22-1
Molecular Formula:C₂₇H₂₄N₄O₂
Molecular Weight:436.513
Hs Code.:

Synonyms:(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

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Chemical Property of (1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

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Technology Process of (1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

There total 13 articles about (1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester 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: 86.0%

: C₁₀H₁₆N₄O₄*ClH

: 100-44-7
benzyl chloride

: 187227-22-1
(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

Guidance literature:: C₁₀H₁₆N₄O₄*ClH; With triethylamine; In methanol; at 0 - 20 ℃; for 3h;

benzyl chloride; With sulfuryl dichloride; triethylamine; at 0 - 20 ℃; for 22h;

Reference yield:

: 187226-89-7
(3R,4S,5R)-5-Azido-4-hydroxy-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

: 187227-22-1
(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / triethylamine; CH₂Cl₂ / 0.75 h / 0 °C

2: 1.) PPh₃, 2.) Et₃N / 1.) THF, rt, 3 h, rt, 2.) H₂O, THF, rt, 12 h

3: 2.95 g / NaN₃, NH₄Cl / dimethylformamide / 21 h / 65 - 70 °C

4: 99 percent / HCl / methanol / 4 h / Ambient temperature

5: 1.) Et₃N, 2.) MeSO₂Cl, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h; rt, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; rt 22 h

With hydrogenchloride; sodium azide; ammonium chloride; methanesulfonyl chloride; triethylamine; triphenylphosphine; In methanol; dichloromethane; triethylamine; N,N-dimethyl-formamide;
DOI:10.1021/ja963036t

Reference yield:

: 187226-95-5
(3R,4R,5S)-4-Amino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

: 187227-22-1
(1S,5S,6S)-5-Azido-7-trityl-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / HCl / methanol / 4 h / Ambient temperature

2: 1.) Et₃N, 2.) MeSO₂Cl, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h; rt, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; rt 22 h

With hydrogenchloride; methanesulfonyl chloride; triethylamine; In methanol;
DOI:10.1021/ja963036t