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

Base Information

• Chemical Name: (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine
• CAS No.: 1609168-90-2
• Molecular Formula: C₂₆H₃₁NO₇
• Molecular Weight: 469.535

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 2 articles about (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine 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:

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate + acetic anhydride (108-24-7) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine (1609168-90-2) + (R,R,R,R)-N(1)-benzyl-2-(acetoxymethyl)-3-benzyloxy-4,5-diacetoxypiperidine (1609168-91-3)

Guidance literature:

(1S,2R,3R,4R,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate; With water; In 1,4-dioxane; at 20 ℃; for 16h;

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 16h;

acetic anhydride; With pyridine; dmap; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tet.2014.03.100

Reference yield:

(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol (1429412-85-0) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine (1609168-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iodine; sodium hydrogencarbonate; acetonitrile / 16 h / 20 °C

2.1: dichloromethane / 1 h / 20 °C

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

3.2: 16 h / 0 - 20 °C

3.3: 16 h / 0 - 20 °C

With water; iodine; sodium hydrogencarbonate; acetonitrile; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.tet.2014.03.100

Reference yield: 100.0%

(2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine (1609168-90-2) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine (1609168-89-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2014.03.100

upstream raw materials:

acetic anhydride

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

Downstream raw materials:

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

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

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

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