(+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane

Base Information

• Chemical Name: (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane
• CAS No.: 74212-25-2
• Molecular Formula: C₁₆H₂₃NO₅S
• Molecular Weight: 341.428
• Mol file: 74212-25-2.mol

Synonyms:(+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane

Chemical Property of (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane

There total 18 articles about (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane 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: 95.0%

(3aR,4S,6R,6aS)-2,2-Dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-cyclopenta[1,3]dioxole-4-carboxylic acid methyl ester (74212-24-1) → (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane (74212-25-2)

Guidance literature:

With calcium borohydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)71394-3

Reference yield:

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester (133344-08-8) → (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane (74212-25-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 94 percent / NMO / OsO₄ / acetone; tetrahydrofuran / 1 h / 25 °C

2: 98 percent / TsOH / acetone / 0.25 h / 25 °C

3: 96 percent / 10percent aq. NaOH / methanol / 25 °C

4: 100 percent / SOCl₂ / 0.25 h / Heating

5: 89 percent / aq. NaN₃, tetramethyl ammonium bromide / CH₂Cl₂ / 25 °C

6: 100 percent / toluene / 0.5 h / Heating

7: 76 percent / toluene / 2 h / Heating

8: H₂ / 10percent Pd/C / methanol / 25 °C

9: NaBH₄ / methanol / 25 °C

With sodium hydroxide; sodium tetrahydroborate; thionyl chloride; sodium azide; N-methyl-2-indolinone; hydrogen; tetramethylammonium bromide; palladium on activated charcoal; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4039(00)97035-7

Reference yield:

(1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester → (+/-)-1-(4-toluenesulfonyl)amino-4-hydroxymethyl-2,3-isopropylidenedioxycyclopentane (74212-25-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / TsOH / acetone / 0.25 h / 25 °C

2: 96 percent / 10percent aq. NaOH / methanol / 25 °C

3: 100 percent / SOCl₂ / 0.25 h / Heating

4: 89 percent / aq. NaN₃, tetramethyl ammonium bromide / CH₂Cl₂ / 25 °C

5: 100 percent / toluene / 0.5 h / Heating

6: 76 percent / toluene / 2 h / Heating

7: H₂ / 10percent Pd/C / methanol / 25 °C

8: NaBH₄ / methanol / 25 °C

With sodium hydroxide; sodium tetrahydroborate; thionyl chloride; sodium azide; hydrogen; tetramethylammonium bromide; palladium on activated charcoal; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4039(00)97035-7

upstream raw materials:

(3aR,4S,6R,6aS)-2,2-Dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-cyclopenta[1,3]dioxole-4-carboxylic acid methyl ester

Tosyl isocyanate

Methyl N-(p-tolylsulfonyl)iminoacetate

(1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester