Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester
• CAS No.: 81691-18-1
• Molecular Formula: C₁₉H₂₈O₇S
• Molecular Weight: 400.493
• Mol file: 81691-18-1.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester

There total 4 articles about Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester 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: 88.0%

4-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-butan-2-ol (81691-14-7,81691-15-8) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester (81691-17-0,81691-18-1)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/S0008-6215(00)81033-2

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester (81691-17-0,81691-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / toluene / 1.) room temp., overnight, 2.) 60 deg C, 2 h.

2: 95 percent / sodium borohydride / ethanol / 0.08 h

3: 100 percent / 10percent palladium-on-charcoal / ethanol

4: 88 percent / pyridine / 0 °C

With pyridine; sodium tetrahydroborate; palladium on activated charcoal; In ethanol; toluene;

DOI:10.1016/S0008-6215(00)81033-2

Reference yield:

methyl (E)-5,6,8-trideoxy-2,3-O-isopropylene-β-D-ribo-oct-5-eno-1,4-furanosid-7-ulose (69984-01-6,72704-88-2) → Toluene-4-sulfonic acid 3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1-methyl-propyl ester (81691-17-0,81691-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / sodium borohydride / ethanol / 0.08 h

2: 100 percent / 10percent palladium-on-charcoal / ethanol

3: 88 percent / pyridine / 0 °C

With pyridine; sodium tetrahydroborate; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0008-6215(00)81033-2

upstream raw materials:

4-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-butan-2-ol

p-toluenesulfonyl chloride

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

(E)-4-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-en-2-ol

Downstream raw materials:

Toluene-4-sulfonic acid 3-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-1-methyl-propyl ester