2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester
• CAS No.: 174272-12-9
• Molecular Formula: C₂₁H₂₉NO₇S
• Molecular Weight: 439.53
• Mol file: 174272-12-9.mol

Synonyms:2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl 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: 96.5%

2,2-dimethoxy-propane (77-76-9) + 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose (163356-94-3) → 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-7-yl ester (174272-12-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 1h; Heating;

DOI:10.1016/0008-6215(95)00261-8

Reference yield: 93.5%

2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-7-yl ester (174272-12-9) → 1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-altropyranose (174272-13-0)

Guidance literature:

With sodium hydroxide; In methanol; for 13.5h; Ambient temperature;

DOI:10.1016/0008-6215(95)00261-8

Reference yield:

2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-7-yl ester (174272-12-9) → D-ribo-phytosphingosine (554-62-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 93.5 percent / aq. NaOH / methanol / 13.5 h / Ambient temperature

2: 96.2 percent / (COCl)2, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2.5 h / -78 °C

3: 1.) AcOOH, AcOH, 2.) Me₂S, 3.) conc. HCl

4: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

5: 96.3 percent / p-TsOH*H₂O / toluene / 1 h / Heating

6: 97.3 percent / NaBH₄ / tetrahydrofuran; ethanol; H₂O / 2 h / Ambient temperature

7: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 38.5 h / Ambient temperature

8: 89.3 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

9: 74.5 percent / Pr₄NRuO₄, N-methylmorpholine-N-oxide, MS 4Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

10: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h

11: 99.5 percent / H₂ / 10percent Pd/C / ethyl acetate / Ambient temperature

12: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature

13: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH₄ / ethanol; H₂O / 10 h / Ambient temperature; Irradiation

With 1H-imidazole; hydrogenchloride; peracetic acid; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; dimethylsulfide; MS 4Angstroem; 1,5-dimethoxynaphthalene; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(95)00261-8

upstream raw materials:

2,2-dimethoxy-propane

1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

Downstream raw materials:

1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-altropyranose

D-ribo-phytosphingosine

(2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide

1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-ribo-hexopyranos-2-ulose