(S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester
• CAS No.: 116185-59-2
• Molecular Formula: C₃₇H₄₇NO₉
• Molecular Weight: 649.781
• Mol file: 116185-59-2.mol

Synonyms:

Chemical Property of (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester

There total 6 articles about (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl 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:

(R)-2,3-cyclohexylideneglyceraldehyde (78008-36-3) → (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester (116185-59-2,116185-67-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / diethyl ether / -78 °C

2: 84 percent / dimsyl sodium / dimethylsulfoxide / Ambient temperature

3: 90 percent / Na, liquid NH₃ / tetrahydrofuran

4: 78 percent / Celite, 3M Jones' reagent / tetrahydrofuran / 1 h / 0 °C

5: 98 percent / (COCl)2 / benzene / 1 h / 5 - 22 °C

6: 1.) isopropylmagnesium chloride / 1.) THF, from -10 to 0 deg C, 40 min, 2.)

With jones' reagent; oxalyl dichloride; Celite; ammonia; isopropylmagnesium chloride; sodium; sodium methylsulfinylmethanide; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; benzene;

DOI:10.1021/jo00254a060

Reference yield:

(1R,2R,S,4R)-5-(benzyloxy)-1-(2,2-pentamethylene-1,3-dioxolan-4-yl)-4-methylpentan-2-ol (116185-65-0,116296-67-4,136457-94-8) → (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester (116185-59-2,116185-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / dimsyl sodium / dimethylsulfoxide / Ambient temperature

2: 90 percent / Na, liquid NH₃ / tetrahydrofuran

3: 78 percent / Celite, 3M Jones' reagent / tetrahydrofuran / 1 h / 0 °C

4: 98 percent / (COCl)2 / benzene / 1 h / 5 - 22 °C

5: 1.) isopropylmagnesium chloride / 1.) THF, from -10 to 0 deg C, 40 min, 2.)

With jones' reagent; oxalyl dichloride; Celite; ammonia; isopropylmagnesium chloride; sodium; sodium methylsulfinylmethanide; In tetrahydrofuran; dimethyl sulfoxide; benzene;

DOI:10.1021/jo00254a060

Reference yield:

(1R,2R,S,4R)-5-(benzyloxy)-1-(2,2-pentamethylene-1,3-dioxolan-4-yl)-2-methoxy-4-methylpentane (116185-66-1,136457-98-2) → (S)-1-((Z)-(4R,6S)-2-Benzyloxycarbonyl-6-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-3-hydroxy-6-methoxy-4-methyl-hex-2-enoyl)-piperidine-2-carboxylic acid benzyl ester (116185-59-2,116185-67-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Na, liquid NH₃ / tetrahydrofuran

2: 78 percent / Celite, 3M Jones' reagent / tetrahydrofuran / 1 h / 0 °C

3: 98 percent / (COCl)2 / benzene / 1 h / 5 - 22 °C

4: 1.) isopropylmagnesium chloride / 1.) THF, from -10 to 0 deg C, 40 min, 2.)

With jones' reagent; oxalyl dichloride; Celite; ammonia; isopropylmagnesium chloride; sodium; In tetrahydrofuran; benzene;

DOI:10.1021/jo00254a060

upstream raw materials:

(2R,4S)-4-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-4-methoxy-2-methyl-butyryl chloride

(S)-1-(2-Benzyloxycarbonyl-acetyl)-piperidine-2-carboxylic acid benzyl ester

(R)-2,3-cyclohexylideneglyceraldehyde

(1R,2R,S,4R)-5-(benzyloxy)-1-(2,2-pentamethylene-1,3-dioxolan-4-yl)-4-methylpentan-2-ol