(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol
• CAS No.: 1413399-55-9
• Molecular Formula: C₃₁H₃₇NO₄
• Molecular Weight: 487.639

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol

Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol

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Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol

There total 1 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol 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: 92.0%

D‐arabino‐nitrone + bromopentene (1119-51-3) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol (1413399-55-9)

Guidance literature:

bromopentene; With iodine; magnesium; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;

D‐arabino‐nitrone; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1021/jo4010553

Reference yield:

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol (1413399-55-9) → 1-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-yl)ethanone (1413399-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: copper diacetate; acetic acid; zinc / dichloromethane / 6 h

2: sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C

With copper diacetate; sodium hydrogencarbonate; acetic acid; zinc; In dichloromethane;

DOI:10.1021/jo4010553

Reference yield:

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-ol (1413399-55-9) → C31H37NO3

Guidance literature:

With copper diacetate; acetic acid; zinc; In dichloromethane; for 6h;

DOI:10.1021/jo4010553

upstream raw materials:

bromopentene

Downstream raw materials:

(3S,4S,4aR)-3-(6-((2R,3R,4R,5R)-1-acetyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-yl)hex-2-en-1-yl)-4-(benzhydryloxy)hexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one

1-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(pent-4-en-1-yl)pyrrolidin-1-yl)ethanone

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