(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol
CAS No.:392663-05-7
Molecular Formula:C₁₆H₂₃IO₄
Molecular Weight:406.261
Hs Code.:

Synonyms:(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

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Chemical Property of (2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

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Technology Process of (2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

There total 4 articles about (2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-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: 70.0%

: 392663-03-5
(E)-(2R,4S,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol

: 392663-05-7
(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Guidance literature:: With N-iodo-succinimide; sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 2.5h;
DOI:10.1002/1521-3773(20011105)40

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 392663-05-7
(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

With N-iodo-succinimide; lithium aluminium tetrahydride; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; In tetrahydrofuran; diethyl ether; water; acetonitrile;
DOI:10.1021/ja0547477

Reference yield:

: 392663-00-2
(E)-(S)-6-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-hex-3-en-2-one

: 392663-05-7
(2R,3S,5R)-2-((1S,2R)-3-Benzyloxy-1-iodo-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

2: 97 percent / AcOH / H₂O / 5 h / 40 °C

3: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

With N-iodo-succinimide; lithium aluminium tetrahydride; sodium hydrogencarbonate; acetic acid; lithium iodide; In tetrahydrofuran; diethyl ether; water;
DOI:10.1021/ja0547477