tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate
• CAS No.: 1321494-57-8
• Molecular Formula: C₁₈H₃₁NO₆
• Molecular Weight: 357.447

Synonyms:tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate

Chemical Property of tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate

There total 22 articles about tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate 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: 75.1%

(1R,7S,8S)-tert-butyl 8-(methoxymethoxy)bicyclo[5.4.0]undec-5-en-1-ylcarbamate (1321494-56-7) → tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate (1321494-57-8)

Guidance literature:

(1R,7S,8S)-tert-butyl 8-(methoxymethoxy)bicyclo[5.4.0]undec-5-en-1-ylcarbamate; With ozone; In methanol; dichloromethane; at -78 ℃;

With triphenylphosphine; In methanol; dichloromethane; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol2018032

Reference yield:

1-(trimethylsilyl)oct-7-en-2-yn-1-ol (1321494-42-1) → tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate (1321494-57-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 - 0 °C / Inert atmosphere

2.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.5 h / 20 °C / Inert atmosphere

3.1: N,N,N,N,-tetramethylethylenediamine / toluene / 0.25 h / 0 °C / Inert atmosphere

4.1: tert.-butyl lithium / diethyl ether; hexane / 0.17 h / -78 - 20 °C / Inert atmosphere

4.2: 0.08 h / -40 °C / Inert atmosphere

4.3: 0.08 h / -78 °C / Inert atmosphere

5.1: tetrachlorobis(tetrahydrofuran)titanium(IV) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

5.2: 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

7.1: pyridine / 0.5 h / 70 °C / Inert atmosphere

8.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 1 h / 70 °C / Inert atmosphere

9.1: methanol; potassium carbonate / 1 h / 50 °C / Inert atmosphere

10.1: 2,4,6-trimethyl-pyridine; N-iodo-succinimide; camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

11.1: borane-THF / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

11.2: 0.5 h / 0 °C / Inert atmosphere

12.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 50 °C / Inert atmosphere

13.1: acetic acid; zinc / 1 h / 20 °C / Inert atmosphere

14.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

14.2: 0.25 h / -78 - 0 °C / Inert atmosphere

15.1: sodium chlorite; sodium phosphate dibasic dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 8 h / 0 - 20 °C

16.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.58 h / 0 °C / Inert atmosphere; Reflux

16.2: 3 h / 20 °C / Inert atmosphere

17.1: ozone / methanol; dichloromethane / -78 °C

17.2: 0.5 h / -78 - 20 °C / Inert atmosphere

With pyridine; Grubbs catalyst first generation; 2,4,6-trimethyl-pyridine; methanol; sodium chlorite; N-iodo-succinimide; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); tetrachlorobis(tetrahydrofuran)titanium(IV); sodium phosphate dibasic dihydrate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 1.2: Swern oxidation / 14.1: Swern oxidation / 14.2: Swern oxidation / 15.1: Kraus oxidation / 16.2: Curtius rearrangement;

DOI:10.1021/ol2018032

Reference yield:

2-(oct-7-en-2-ynyloxy)tetrahydro-2H-pyran → tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate (1321494-57-8)

Guidance literature:

Multi-step reaction with 20 steps

1.1: camphor-10-sulfonic acid / methanol / 3 h / 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere

3.1: N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 - 0 °C / Inert atmosphere

5.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.5 h / 20 °C / Inert atmosphere

6.1: N,N,N,N,-tetramethylethylenediamine / toluene / 0.25 h / 0 °C / Inert atmosphere

7.1: tert.-butyl lithium / diethyl ether; hexane / 0.17 h / -78 - 20 °C / Inert atmosphere

7.2: 0.08 h / -40 °C / Inert atmosphere

7.3: 0.08 h / -78 °C / Inert atmosphere

8.1: tetrachlorobis(tetrahydrofuran)titanium(IV) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.2: 0 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

10.1: pyridine / 0.5 h / 70 °C / Inert atmosphere

11.1: Grubbs catalyst first generation / 1,2-dichloro-ethane / 1 h / 70 °C / Inert atmosphere

12.1: methanol; potassium carbonate / 1 h / 50 °C / Inert atmosphere

13.1: 2,4,6-trimethyl-pyridine; N-iodo-succinimide; camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

14.1: borane-THF / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

14.2: 0.5 h / 0 °C / Inert atmosphere

15.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 50 °C / Inert atmosphere

16.1: acetic acid; zinc / 1 h / 20 °C / Inert atmosphere

17.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

17.2: 0.25 h / -78 - 0 °C / Inert atmosphere

18.1: sodium chlorite; sodium phosphate dibasic dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 8 h / 0 - 20 °C

19.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.58 h / 0 °C / Inert atmosphere; Reflux

19.2: 3 h / 20 °C / Inert atmosphere

20.1: ozone / methanol; dichloromethane / -78 °C

20.2: 0.5 h / -78 - 20 °C / Inert atmosphere

With pyridine; Grubbs catalyst first generation; 2,4,6-trimethyl-pyridine; methanol; sodium chlorite; N-iodo-succinimide; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); tetrachlorobis(tetrahydrofuran)titanium(IV); sodium phosphate dibasic dihydrate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 3.1: retro-Brook rearrangement / 4.1: Swern oxidation / 4.2: Swern oxidation / 17.1: Swern oxidation / 17.2: Swern oxidation / 18.1: Kraus oxidation / 19.2: Curtius rearrangement;

DOI:10.1021/ol2018032

upstream raw materials:

1-(trimethylsilyl)oct-7-en-2-yn-1-ol

1-(trimethylsilyl)oct-7-en-2-yn-1-one

(S)-1-(trimethylsilyl)oct-7-en-2-yn-1-ol

(S)-1-(trimethylsilyl)oct-7-en-2-ynyl methanesulfonate

Downstream raw materials:

tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate

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