(2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol

Base Information

• Chemical Name: (2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol
• CAS No.: 108867-40-9
• Molecular Formula: C₁₇H₂₄O₅S
• Molecular Weight: 340.441
• Mol file: 108867-40-9.mol

Synonyms:(2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol

Chemical Property of (2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol

There total 1 articles about (2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol 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: 93.0%

(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (88424-94-6) + p-toluenesulfonyl chloride (98-59-9) → (2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol (108867-40-9)

Guidance literature:

With dmap; In pyridine; for 2h; Ambient temperature;

DOI:10.1021/jo00226a011

Reference yield:

(2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol (108867-40-9) → (2R,3R,4R)-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol (108867-41-0)

Guidance literature:

With trifluoroacetic acid; In methanol; water; for 48h; Ambient temperature;

DOI:10.1021/jo00226a011

Reference yield:

(2R,3R,4R)-1,2-O-isopropylidene-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol (108867-40-9) → (2S,3R,4S)-3-(benzyloxy)-2,4-dimethyl-5-(trityloxy)pentanal (108817-30-7)

Guidance literature:

Multi-step reaction with 6 steps

1: trifluoroacetic acid / methanol; H₂O / 48 h / Ambient temperature

2: 64 percent / NaOCH₃ / methanol / 0.5 h / 22 °C

3: 71 percent / CuCN / diethyl ether / 15 h / Ambient temperature

4: 93 percent / DMAP / pyridine / 5 h / 22 °C

5: 90 percent / NaH / dimethylformamide / 22 h / 50 °C

6: 1.) O₃, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 2.) MeOH, 30 min

With dmap; dimethylsulfide; sodium methylate; sodium hydride; ozone; trifluoroacetic acid; In pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00226a011

upstream raw materials:

(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

p-toluenesulfonyl chloride

Downstream raw materials:

(2R,3R,4R)-4-methyl-3-O-tosylhex-5-ene-1,2,3-triol

(2S,3R,4S)-3-(benzyloxy)-2,4-dimethyl-5-(trityloxy)pentanal

(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

(2S,3S,4R)-2,4-dimethyl-1-O-tritylhex-5-ene-1,3-diol