(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride

Base Information

• Chemical Name: (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride
• CAS No.: 1609168-92-4
• Molecular Formula: C₂₀H₂₅NO₄*ClH
• Molecular Weight: 379.884
• Mol file: 1609168-92-4.mol

Synonyms:(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride

Chemical Property of (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride

There total 5 articles about (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride 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: 100.0%

(2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine (1609168-89-9) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride (1609168-92-4)

Guidance literature:

With hydrogenchloride; In diethyl ether; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tet.2014.03.100

Reference yield:

(R,R,R,R)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine (1429412-90-7) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride (1609168-92-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dichloromethane / 1 h / 20 °C

2.1: water / 1,4-dioxane / 16 h / 20 °C

2.2: 16 h / 0 - 20 °C

3.1: hydrogenchloride / diethyl ether / 0.17 h / 20 °C

With hydrogenchloride; water; In 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2014.03.100

Reference yield:

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride (1609168-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water / 1,4-dioxane / 16 h / 20 °C

1.2: 16 h / 0 - 20 °C

2.1: hydrogenchloride / diethyl ether / 0.17 h / 20 °C

With hydrogenchloride; water; In 1,4-dioxane; diethyl ether;

DOI:10.1016/j.tet.2014.03.100

upstream raw materials:

(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine

(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol

(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine

(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine

Downstream raw materials:

2,5-anhydro-2,5-imino-D-glucitol