(R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one

Base Information

• Chemical Name: (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one
• CAS No.: 154840-40-1
• Molecular Formula: C₁₆H₁₉IO₄
• Molecular Weight: 402.229

Synonyms:(R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one

Chemical Property of (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one

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Technology Process of (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one

There total 2 articles about (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one 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: 70.0%

Carbonic acid (Z)-(1R,2S)-1-benzyloxymethyl-4-iodo-2-methyl-5-pent-4-enyloxy-hex-3-enyl ester tert-butyl ester → (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one (154840-40-1)

Guidance literature:

With iodonium di-sym-collidine tetrafluoroborate; In chloroform; at 0 ℃; for 72h;

DOI:10.1016/0040-4039(93)85057-4

Reference yield:

(2R,3S)-1-Benzyloxy-3-methyl-6-pent-4-enyloxy-hept-4-yn-2-ol → (R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one (154840-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-Bu₃SnH, AIBN, 2.) n-BuLi; 3.) I₂ / 1.) 120 deg C, 3 h; 2.) 0 deg C, 10 min then rt.; acetonitrile, -20 deg C, 15 min

2: 70 percent / I(collidine)2⁽¹⁺⁾*BF₄^(1-) / CHCl₃ / 72 h / 0 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); iodonium di-sym-collidine tetrafluoroborate; iodine; tri-n-butyl-tin hydride; In chloroform;

DOI:10.1016/0040-4039(93)85057-4

Reference yield:

(R)-4-((Z)-(1R,2R)-2-Benzyloxy-3-iodo-1-methyl-pent-3-enyl)-[1,3]dioxolan-2-one (154840-40-1) → (Z)-(2R,3R,4S)-4-Benzyloxy-3-methyl-hept-5-ene-1,2-diol + (E)-(2R,3R,4S)-4-Benzyloxy-3-methyl-hept-5-ene-1,2-diol

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(93)85057-4

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