(4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane

Base Information

• Chemical Name: (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane
• CAS No.: 140385-63-3
• Molecular Formula: C₁₄H₁₉NO₂Se
• Molecular Weight: 312.27
• Mol file: 140385-63-3.mol

Synonyms:(4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane

Chemical Property of (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane

There total 34 articles about (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane 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%

racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone (85365-61-3,98717-29-4) → 1-(phenylseleno)platynecine (85365-59-9,98675-04-8,140385-63-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 2h;

DOI:10.1246/cl.1983.125

Reference yield: 84.0%

5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone (85365-61-3,98717-29-4) → (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane (140385-63-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)89003-7

Reference yield:

7-Oxo-8α-pyrrolizidin-1α-carbonsaeure-methylester (25471-73-2) → (4R,5S,6R)-6-hydroxy-4-(hydroxymethyl)-4-(phenylseleno)-1-azabicyclo<3.3.0>octane (140385-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / PtO₂ / methanol / 1.5 h / 760 Torr / Ambient temperature

2: 75 percent / EtONa, 3-A molecular sieve / ethanol / 2.5 h / Heating

3: 1.) LDA / 1.) THF, -70 deg C, 1.5 h, 2.) a) THF, -70 deg C, 1 h, b) -40 deg C, 1.5 h

4: LiAlH₄ / tetrahydrofuran / 3 h / -35 °C

With lithium aluminium tetrahydride; 3 A molecular sieve; hydrogen; sodium ethanolate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jo00223a002

upstream raw materials:

5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

7-Oxo-8α-pyrrolizidin-1α-carbonsaeure-methylester

(1R,7S,7aR)-7-Hydroxy-hexahydro-pyrrolizine-1-carboxylic acid methyl ester

(1R,7R,7aR)-7-Hydroxy-hexahydro-pyrrolizine-1-carboxylic acid methyl ester

Downstream raw materials:

(-)-integerrimine