4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one

Base Information

• Chemical Name: 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one
• CAS No.: 929905-84-0
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

Synonyms:4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one

Chemical Property of 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one

Chemical Property:

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Technology Process of 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one

There total 3 articles about 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-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: 77.0%

(3S,4R)-3-benzyloxy-1-hydroxy-4,5-isopropylidenedioxypentan-2-one (929905-83-9) + trimethyl phosphonoacetate (5927-18-4) → 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one (929905-84-0) + (Z)-methyl (4R,5R)-4-benzyloxy-3-hydroxymethyl-5,6-isopropylidenedioxy-hex-2-enoate (929905-85-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -50 - 0 ℃;

DOI:10.1055/s-2006-951540

Reference yield: 73.0%

methyl (4R,5R)-4-benzyloxy-3-tert-butyldiphenylsilyloxymethyl-5,6-isopropylidenedioxy-hex-2-enoate → 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one (929905-84-0) + (Z)-methyl (4R,5R)-4-benzyloxy-3-hydroxymethyl-5,6-isopropylidenedioxy-hex-2-enoate (929905-85-1)

Guidance literature:

methyl (4R,5R)-4-benzyloxy-3-tert-butyldiphenylsilyloxymethyl-5,6-isopropylidenedioxy-hex-2-enoate; With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 25 ℃; Inert atmosphere;

With water; In tetrahydrofuran; Inert atmosphere;

DOI:10.1016/j.tet.2008.11.079

Reference yield: 10.0%

(3S,4R)-3-benzyloxy-1-hydroxy-4,5-isopropylidenedioxypentan-2-one (929905-83-9) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → 4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-furan-2(5H)-one (929905-84-0) + (Z)-methyl (4R,5R)-4-benzyloxy-3-hydroxymethyl-5,6-isopropylidenedioxy-hex-2-enoate (929905-85-1)

Guidance literature:

In toluene; for 48h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2008.11.079

upstream raw materials:

(3S,4R)-3-benzyloxy-1-hydroxy-4,5-isopropylidenedioxypentan-2-one

trimethyl phosphonoacetate

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

4-((1'R,2'R)-1'-benzyloxy-2',3'-dihydroxypropyl)-furan-2(5H)-one

4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-3-(1''-hydroxyoctyl)-furan-2(5H)-one

4-((1'R,2'R)-1'-benzyloxy-2',3'-isopropylidenedioxy-propyl)-3-(1''-hydroxyhexyl)-furan-2(5H)-one

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