(2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine

Base Information

• Chemical Name: (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine
• CAS No.: 209003-97-4
• Molecular Formula: C₃₃H₄₉NO₄
• Molecular Weight: 523.756

Synonyms:(2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine

Chemical Property of (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine

There total 14 articles about (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine 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:

(2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-87-2) → (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine (209003-97-4)

Guidance literature:

Multi-step reaction with 13 steps

1: NaBH₄ / ethanol / -78 °C

2: 98 percent / NaH, N(Bu₄)I / tetrahydrofuran / Ambient temperature

3: 78 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O / Ambient temperature

4: diethyl ether / Ambient temperature

5: PDC / CH₂Cl₂ / Ambient temperature

6: 1.) CF₃COOH / 1.) ClCH₂CH₂Cl, rt.; 2.) water

7: 1.) AgBF₄; 2.) Zn(BH₄)2 / 1.) THF, -78 deg C

8: 86 percent / tetrahydrofuran / Ambient temperature

9: thionyl chloride / tetrahydrofuran / Ambient temperature

10: KCN / dimethylsulfoxide; tetrahydrofuran

11: 83 percent / DMAP / CH₂Cl₂ / Ambient temperature

12: O₃ / CH₂Cl₂; methanol / -78 °C

13: NaBH₄

With dmap; potassium cyanide; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; silver tetrafluoroborate; thionyl chloride; zinc(II) tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00646-7

Reference yield:

(2R,4R,1'S)-2-(1'-benzyloxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-89-4) → (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine (209003-97-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 78 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O / Ambient temperature

2: diethyl ether / Ambient temperature

3: PDC / CH₂Cl₂ / Ambient temperature

4: 1.) CF₃COOH / 1.) ClCH₂CH₂Cl, rt.; 2.) water

5: 1.) AgBF₄; 2.) Zn(BH₄)2 / 1.) THF, -78 deg C

6: 86 percent / tetrahydrofuran / Ambient temperature

7: thionyl chloride / tetrahydrofuran / Ambient temperature

8: KCN / dimethylsulfoxide; tetrahydrofuran

9: 83 percent / DMAP / CH₂Cl₂ / Ambient temperature

10: O₃ / CH₂Cl₂; methanol / -78 °C

11: NaBH₄

With dmap; potassium cyanide; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; silver tetrafluoroborate; thionyl chloride; zinc(II) tetrahydroborate; ozone; trifluoroacetic acid; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00646-7

Reference yield:

(2R,4R,1'R)-2-(1'-benzyloxy-4'-oxobutyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-90-7) → (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine (209003-97-4)

Guidance literature:

Multi-step reaction with 10 steps

1: diethyl ether / Ambient temperature

2: PDC / CH₂Cl₂ / Ambient temperature

3: 1.) CF₃COOH / 1.) ClCH₂CH₂Cl, rt.; 2.) water

4: 1.) AgBF₄; 2.) Zn(BH₄)2 / 1.) THF, -78 deg C

5: 86 percent / tetrahydrofuran / Ambient temperature

6: thionyl chloride / tetrahydrofuran / Ambient temperature

7: KCN / dimethylsulfoxide; tetrahydrofuran

8: 83 percent / DMAP / CH₂Cl₂ / Ambient temperature

9: O₃ / CH₂Cl₂; methanol / -78 °C

10: NaBH₄

With dmap; potassium cyanide; sodium tetrahydroborate; dipyridinium dichromate; silver tetrafluoroborate; thionyl chloride; zinc(II) tetrahydroborate; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00646-7

upstream raw materials:

(2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-vinylpiperidine

(2S,3R,6S)-3-benzyloxy-6-dodecyl-2-vinylpiperidine

(2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

(3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine

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