(2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether

Base Information

• Chemical Name: (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether
• CAS No.: 86535-08-2
• Molecular Formula: C₁₈H₂₈O₃
• Molecular Weight: 292.419
• Mol file: 86535-08-2.mol

Synonyms:

Chemical Property of (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether

There total 16 articles about (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether 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:

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)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether (86535-08-2)

Guidance literature:

Multi-step reaction with 13 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

With potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; toluene-4-sulfonic acid; sodium nitrite; In pyridine; hydrogenchloride; methanol; diethyl ether; sulfuric acid; water; dimethyl sulfoxide;

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

Reference yield:

(2R,3R)-(-)-threo-3-methylaspartic acid (86562-29-0) → (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether (86535-08-2)

Guidance literature:

Multi-step reaction with 12 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

With potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; toluene-4-sulfonic acid; sodium nitrite; In pyridine; hydrogenchloride; methanol; diethyl ether; sulfuric acid; water; dimethyl sulfoxide;

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

Reference yield:

(2R,3S)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether (81422-90-4) → (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether (86535-08-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / pyridine / 0 - 5 °C

2: 73 percent / KOH / methanol / 0.58 h / 0 - 17 °C

3: 87 percent / CuI / diethyl ether / -55 - -20 °C

4: p-TsOH / diethyl ether / Ambient temperature

With potassium hydroxide; copper(l) iodide; toluene-4-sulfonic acid; In pyridine; methanol; diethyl ether;

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

upstream raw materials:

benzyl chloride

(2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentanol

3,4-dihydro-2H-pyran

methyl (2R,3R)-2-methyl-3-tetrahydropyranyloxypentenoate

Downstream raw materials:

(2S,3R)-2-methylpentane-1,3-diol 1-benzyl ether

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

(2S,3S)-3-Tetrahydropyranyloxy-2-methylpentan-1-ol

(2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether