(2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate

Base Information

• Chemical Name: (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate
• CAS No.: 86535-06-0
• Molecular Formula: C₁₉H₂₄O₅S
• Molecular Weight: 364.463
• Mol file: 86535-06-0.mol

Synonyms:(2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate

Chemical Property of (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate

There total 11 articles about (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate 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: 94.0%

(2R,3S)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether (81422-90-4) + p-toluenesulfonyl chloride (98-59-9) → (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate (86535-06-0)

Guidance literature:

In pyridine; at 0 - 5 ℃;

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) → (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate (86535-06-0)

Guidance literature:

Multi-step reaction with 10 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

With 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) → (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate (86535-06-0)

Guidance literature:

Multi-step reaction with 9 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

With 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

upstream raw materials:

(S)-4-Benzyloxy-3-methyl-butane-1,2-diol

p-toluenesulfonyl chloride

(2R,3S)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether

(2R,3R)-(-)-threo-3-methylaspartic acid

Downstream raw materials:

(2S,3R)-3,4-epoxy-2-methyl-1-butanol benzyl ether

(-)-serricornin

(4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone

serricornin acetate <(4S,6R,7R)-4,6-dimethyl-7-acetoxy-3-nonanone>