1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene

Base Information

• Chemical Name: 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene
• CAS No.: 221184-12-9
• Molecular Formula: C₃₆H₃₈O₅
• Molecular Weight: 550.695

Synonyms:1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene

Chemical Property of 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene

Chemical Property:

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Technology Process of 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene

There total 4 articles about 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene 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: 67.0%

4-Methoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester (221184-11-8) + 1,1-dibromomethane (74-95-3) → 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene (221184-12-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc;

DOI:10.1021/jo982331o

Reference yield:

3,4,6-tri-O-benzyl-β-D-arabinofuranoside (60933-68-8) → 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene (221184-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / tetrahydrofuran

2: 92 percent / DMAP, DCC

3: 67 percent / TiCl₄, Zn, TMEDA, PbCl₂

With dmap; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; dicyclohexyl-carbodiimide; lead(II) chloride; zinc; In tetrahydrofuran;

DOI:10.1021/jo982331o

Reference yield:

(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene (102208-53-7) → 1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene (221184-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAP, DCC

2: 67 percent / TiCl₄, Zn, TMEDA, PbCl₂

With dmap; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; dicyclohexyl-carbodiimide; lead(II) chloride; zinc;

DOI:10.1021/jo982331o

upstream raw materials:

4-Methoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester

1,1-dibromomethane

3,4,6-tri-O-benzyl-β-D-arabinofuranoside

4-methoxybenzoic acid

Downstream raw materials:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol

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