Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI)

Base Information

• Chemical Name: Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI)
• CAS No.: 141208-49-3
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Mol file: 141208-49-3.mol

Synonyms:Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI)

Chemical Property of Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI)

There total 7 articles about Cyclobutanecarboxylic acid, 2,3-bis(hydroxymethyl)-, [1S-(1alpha,2alpha,3beta)]- (9CI) 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:

(1RS,2R,3S)-2,3-bisbenzyloxymethylcyclobutane-1-carboxylic acid (141208-48-2,141271-20-7,150521-40-7) → (1RS,2R,3S)-2,3-bishydroxymethylcyclobutane-1-carboxylic acid (141208-49-3,141271-21-8,150521-41-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h;

DOI:10.1016/S0040-4020(01)88715-9

Reference yield:

(3S,4S)-3,4-bishydroxymethyl-1-methylidenecyclopentane (138804-28-1) → (1RS,2R,3S)-2,3-bishydroxymethylcyclobutane-1-carboxylic acid (141208-49-3,141271-21-8,150521-41-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, r.t., 2.) DMF, r.t., overnight

2: 78.3 percent / NaIO₄, OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 6 h / Ambient temperature

3: 1.) NaOEt, HCOOEt, 2.) Et₃N, TsN₃ / 1.) THF, 3 h, r.t., 2.) CH₂Cl₂, overnight, r.t.

4: 30 - 40 °C / Irradiation

5: KOH / methanol / a) r.t., 22 h, b) 45 deg C, 4 h

6: H₂ / 10percent Pd/C / methanol / 4 h

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; 4-toluenesulfonyl azide; hydrogen; sodium ethanolate; sodium hydride; triethylamine; formic acid ethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)88715-9

Reference yield:

(3S,4S)-3,4-bisbenzyloxymethyl-1-methylidenecyclopentane (141208-43-7) → (1RS,2R,3S)-2,3-bishydroxymethylcyclobutane-1-carboxylic acid (141208-49-3,141271-21-8,150521-41-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 78.3 percent / NaIO₄, OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 6 h / Ambient temperature

2: 1.) NaOEt, HCOOEt, 2.) Et₃N, TsN₃ / 1.) THF, 3 h, r.t., 2.) CH₂Cl₂, overnight, r.t.

3: 30 - 40 °C / Irradiation

4: KOH / methanol / a) r.t., 22 h, b) 45 deg C, 4 h

5: H₂ / 10percent Pd/C / methanol / 4 h

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; 4-toluenesulfonyl azide; hydrogen; sodium ethanolate; triethylamine; formic acid ethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)88715-9

upstream raw materials:

(1RS,2R,3S)-2,3-bisbenzyloxymethylcyclobutane-1-carboxylic acid

(3S,4S)-3,4-bishydroxymethyl-1-methylidenecyclopentane

(3S,4S)-3,4-bisbenzyloxymethyl-1-methylidenecyclopentane

(3S,4S)-3,4-bisbenzyloxymethyl-1-cyclopentanone

Refernces