N,N'-bis<(1R,6S,7R,8S)-7-formylbicyclo<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-formylbicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide
CAS No.:173737-54-7
Molecular Formula:C₃₇H₅₀N₂O₆S₂
Molecular Weight:682.946
Hs Code.:

Synonyms:N,N'-bis<(1R,6S,7R,8S)-7-formylbicyclo<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-formylbicyclo<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-formylbicyclo<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-formylbicyclo<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: 96.0%

: 173737-45-6
N,N'-bis<(1R,6S,7R,8S)-7-(hydroxymethyl)bicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

: 173737-54-7
N,N'-bis<(1R,6S,7R,8S)-7-formylbicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo951413z

Reference yield:

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

: 173737-54-7
N,N'-bis<(1R,6S,7R,8S)-7-formylbicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: Multi-step reaction with 12 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

11: 97 percent / Raney nickel, H₂ / ethanol / 18 h

12: 96 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

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

Reference yield:

: 158342-55-3
(1R,2R)-diethyl 4-cyclohexene-1,2-diacetate

: 173737-54-7
N,N'-bis<(1R,6S,7R,8S)-7-formylbicyclo<4.3.0>non-8-yl>-N,N'-bis(toluene-4-sulfonyl)-1,3-propanediamide

Guidance literature:: Multi-step reaction with 13 steps

1: 96 percent / NaH / tetrahydrofuran / 2.5 h

2: 99 percent / TsOH*H₂O / benzene / 12 h / Heating

3: 99 percent / LiAlH₄ / diethyl ether / 5 h / Ambient temperature

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

5: 99 percent / aq. HCl / tetrahydrofuran / 3 h / 60 °C

6: 70 percent / NaBH(OAc)3 / tetrahydrofuran; acetic acid / 1) 0-5 deg C, 1 h; 2) room temperature, 24 h

7: 77 percent / NH₄OCHO / Pd/C / methanol / 3 h / Heating

8: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

9: 83 percent / K₂CO₃, KI / acetonitrile / 72 h / Heating

10: 84 percent / sodium bis(methoxyethoxy)aluminum hydride / toluene / 18 h / 100 °C

11: 97 percent / Et₃N / CH₂Cl₂ / 72 h / Ambient temperature

12: 97 percent / Raney nickel, H₂ / ethanol / 18 h

13: 96 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

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