(2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

Base Information

• Chemical Name: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol
• CAS No.: 86535-14-0
• Molecular Formula: C₁₃H₂₀O₄S
• Molecular Weight: 272.365
• Mol file: 86535-14-0.mol

Synonyms:(2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

Chemical Property of (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

There total 21 articles about (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 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: 90.0%

(2S,3S)-2-methylpentane-1,3-diol (149-31-5,94339-79-4,103729-83-5,103729-87-9,121054-24-8,121054-26-0,94953-91-0) + p-toluenesulfonyl chloride (98-59-9) → (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol (86535-14-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86986-6

Reference yield:

(2R,3R)-(-)-threo-3-methylaspartic acid (86562-29-0) → (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol (86535-14-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 50 percent / NaNO₂ / H₂O; H₂SO₄ / 0 - 25 °C

2: diethyl ether

3: p-TsOH / diethyl ether / Ambient temperature

4: 95 percent / LAH / diethyl ether

5: p-TsOH / methanol / Ambient temperature

6: p-TsOH / Ambient temperature

7: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

8: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

9: 94 percent / pyridine / 0 - 5 °C

10: 73 percent / KOH / methanol / 0.58 h / 0 - 17 °C

11: 87 percent / CuI / diethyl ether / -55 - -20 °C

12: p-TsOH / diethyl ether / Ambient temperature

13: H₂ / Pd-C (5percent) / ethanol

14: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

15: p-TsOH / methanol / Ambient temperature

With 3,4-dihydro-2H-pyran; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; toluene-4-sulfonic acid; sodium nitrite; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; sulfuric acid; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(82)80081-1

Reference yield:

D,L-threo-β-methylaspartic acid (642-92-2,1114-07-4,2955-50-2,4846-45-1,5941-19-5,6061-13-8,6667-60-3,7298-96-6,31571-69-4,86562-29-0,121570-10-3,127001-58-5) → (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol (86535-14-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) acetone, MeOH, water; 2.) water, HCl, pH=3, EtOH

2: 50 percent / NaNO₂ / H₂O; H₂SO₄ / 0 - 25 °C

3: diethyl ether

4: p-TsOH / diethyl ether / Ambient temperature

5: 95 percent / LAH / diethyl ether

6: p-TsOH / methanol / Ambient temperature

7: p-TsOH / Ambient temperature

8: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

9: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

10: 94 percent / pyridine / 0 - 5 °C

11: 73 percent / KOH / methanol / 0.58 h / 0 - 17 °C

12: 87 percent / CuI / diethyl ether / -55 - -20 °C

13: p-TsOH / diethyl ether / Ambient temperature

14: H₂ / Pd-C (5percent) / ethanol

15: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

16: p-TsOH / methanol / Ambient temperature

With 3,4-dihydro-2H-pyran; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; toluene-4-sulfonic acid; sodium nitrite; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; sulfuric acid; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(82)80081-1

upstream raw materials:

(2S,3S)-2-methylpentane-1,3-diol

p-toluenesulfonyl chloride

[2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid

(4R,5S)-N-<(2'R,3'S)-3'-hydroxy-2'-methyl-1'-oxopentyl>-4-methyl-5-phenyl-2-oxazolidinone

Downstream raw materials:

(2S,3S)-3-t-butyldimethylsilyloxy-2-methyl-1-(4-methylbenzenesulfonyloxy)pentane

2-methyl-3-pentanol (S)-(-)-MTPA ester

2-methyl-3-pentanol (R)-(+)-MTPA ester

(-)-serricornin