N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Base Information

Chemical Name:N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide
CAS No.:173737-53-6
Molecular Formula:C₅₁H₆₆N₂O₆S₂
Molecular Weight:867.227
Hs Code.:

Synonyms:N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

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Chemical Property of N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

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Technology Process of N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

There total 16 articles about N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide 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: 97.0%

: 98-59-9
p-toluenesulfonyl chloride

: 173737-44-5
N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-1,3-propanediamide

: 173737-53-6
N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: With triethylamine; In dichloromethane; for 72h; Ambient temperature;
DOI:10.1021/jo951413z

Reference yield: 48.0%

: 142-28-9
1,3-Dichloropropane

: 173737-52-5
(1R,6S,7R,8S)-N-(toluene-4-sulfonyl)-7-<(benzyloxy)methyl>bicyclo<4.3.0>nonan-8-amide

: 173737-53-6
N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 48h;
DOI:10.1021/jo951413z

Reference yield:

: 158342-56-4
(1R,6S,7R)-7-(ethoxycarbonyl)bicyclo<4.3.0>non-3-en-8-one

: 173737-53-6
N,N'-bis<(1R,6S,7R,8S)-7-<(benzyloxy)methyl>bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / TsOH*H₂O / benzene / 12 h / Heating

2: 99 percent / LiAlH₄ / diethyl ether / 5 h / Ambient temperature

3: 1.) NaH / 1) DMF, room temperature, 1 h; 2) DMF, room temperature, 22 h

4: 99 percent / aq. HCl / tetrahydrofuran / 3 h / 60 °C

5: 70 percent / NaBH(OAc)3 / tetrahydrofuran; acetic acid / 1) 0-5 deg C, 1 h; 2) room temperature, 24 h

6: 77 percent / NH₄OCHO / Pd/C / methanol / 3 h / Heating

7: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

8: 83 percent / K₂CO₃, KI / acetonitrile / 72 h / Heating

9: 84 percent / sodium bis(methoxyethoxy)aluminum hydride / toluene / 18 h / 100 °C

10: 97 percent / Et₃N / CH₂Cl₂ / 72 h / Ambient temperature

With hydrogenchloride; lithium aluminium tetrahydride; ammonium formate; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; toluene; acetonitrile; benzene;
DOI:10.1021/jo951413z