(2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate
• CAS No.: 1387556-98-0
• Molecular Formula: C₁₉H₃₁N₃O₄S
• Molecular Weight: 397.539
• Mol file: 1387556-98-0.mol

Synonyms:(2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate

Chemical Property of (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate

There total 8 articles about (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate 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:

p-toluenesulfonyl chloride (98-59-9) + [(2R,3R)-3-nonyloxiran-2-yl]methanol (107736-23-2,246545-38-0) → C19H31N3O4S (1387556-99-1) + (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate (1387556-98-0)

Guidance literature:

[(2R,3R)-3-nonyloxiran-2-yl]methanol; With sodium azide; Trimethyl borate; In N,N-dimethyl-formamide; at 50 ℃; for 3h; Inert atmosphere;

p-toluenesulfonyl chloride; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.05.082

Reference yield:

1-undecene (821-95-4) → (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate (1387556-98-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

4.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -25 °C / Inert atmosphere; Molecular sieve

4.2: 24 h / -20 °C

5.1: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere

5.2: 5 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium azide; Trimethyl borate; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; ozone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Wittig reaction / 4.1: Sharpless epoxidation / 4.2: Sharpless epoxidation;

DOI:10.1016/j.bmcl.2012.05.082

Reference yield:

10-Undecen-1-ol (112-43-6) → (2S,3R)-2-azido-3-hydroxydodecyl 4-methylbenzenesulfonate (1387556-98-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux; Inert atmosphere

3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere

6.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -25 °C / Inert atmosphere; Molecular sieve

6.2: 24 h / -20 °C

7.1: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere

7.2: 5 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; sodium azide; Trimethyl borate; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; ozone; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction / 6.1: Sharpless epoxidation / 6.2: Sharpless epoxidation;

DOI:10.1016/j.bmcl.2012.05.082

upstream raw materials:

caprinaldehyde

(2E)-dodec-2-en-1-ol

ethyl (E)-dodec-2-enoate

1-undecene