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

Base Information

• Chemical Name: tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate
• CAS No.: 1321494-58-9
• Molecular Formula: C₂₁H₃₅NO₆
• Molecular Weight: 397.512
• Mol file: 1321494-58-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-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:

tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate (1321494-57-8) + rel-(4R,5R)-4,5-diphenyl-2-(propa-1,2-dienyl)-1,3-ditosyl-1,3,2-diazaborolidine → tert-butyl (1R,2S,3S)-2-formyl-1-((S)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate + tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate (1321494-58-9)

Guidance literature:

tert-butyl (1S,2S,3S)-2-formyl-3-(methoxymethoxy)-1-(4-oxobutyl)cyclohexylcarbamate; rel-(4R,5R)-4,5-diphenyl-2-(propa-1,2-dienyl)-1,3-ditosyl-1,3,2-diazaborolidine; In dichloromethane; at -78 ℃; Inert atmosphere;

With water; In methanol; dichloromethane; at -78 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol2018032

Reference yield:

(S,E)-2-ethynyl-2-(pent-4-enyl)oct-6-enyl acetate (1321494-45-4) → tert-butyl (1R,2S,3S)-2-formyl-1-((S)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate + tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate (1321494-58-9)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3.1: 2,4,6-trimethyl-pyridine; N-iodo-succinimide; camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

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

4.2: 0.5 h / 0 °C / Inert atmosphere

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

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

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

7.2: 0.25 h / -78 - 0 °C / Inert atmosphere

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

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

9.2: 3 h / 20 °C / Inert atmosphere

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

10.2: 0.5 h / -78 - 20 °C / Inert atmosphere

11.1: dichloromethane / -78 °C / Inert atmosphere

11.2: -78 °C / Inert atmosphere

With Grubbs catalyst first generation; 2,4,6-trimethyl-pyridine; methanol; sodium chlorite; N-iodo-succinimide; sodium phosphate dibasic dihydrate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 7.1: Swern oxidation / 7.2: Swern oxidation / 8.1: Kraus oxidation / 9.2: Curtius rearrangement;

DOI:10.1021/ol2018032

Reference yield:

(R)-(bicyclo[5.4.0]undeca-5,7-dien-1-yl)methyl acetate (1321494-47-6) → tert-butyl (1R,2S,3S)-2-formyl-1-((S)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate + tert-butyl (1R,2S,3S)-2-formyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate (1321494-58-9)

Guidance literature:

Multi-step reaction with 10 steps

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

2.1: 2,4,6-trimethyl-pyridine; N-iodo-succinimide; camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

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

3.2: 0.5 h / 0 °C / Inert atmosphere

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

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

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

6.2: 0.25 h / -78 - 0 °C / Inert atmosphere

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

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

8.2: 3 h / 20 °C / Inert atmosphere

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

9.2: 0.5 h / -78 - 20 °C / Inert atmosphere

10.1: dichloromethane / -78 °C / Inert atmosphere

10.2: -78 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; methanol; sodium chlorite; N-iodo-succinimide; sodium phosphate dibasic dihydrate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol; 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Kraus oxidation / 8.2: 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-ethynyl-1-((R)-4-hydroxyhept-6-ynyl)-3-(methoxymethoxy)-cyclohexylcarbamate