methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate

Base Information

• Chemical Name: methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate
• CAS No.: 653565-47-0
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 653565-47-0.mol

Synonyms:methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate

Chemical Property of methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate

There total 3 articles about methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate 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: 80.7%

trimethyl phosphonoacetate (5927-18-4) + [2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde (81577-69-7) → methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate (653565-47-0)

Guidance literature:

trimethyl phosphonoacetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

[2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde; In tetrahydrofuran; at 0 ℃; for 0.366667h;

DOI:10.1021/jo035223x

Reference yield: 45.0%

Acetic acid (2R,4aR,6S,7S,8R,8aR)-6-methoxy-7-(2-nitro-phenylselanyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate (653565-47-0) + methyl-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-erythro-hex-2-enopyranoside + (2R,4aR,8aS)-2-phenyl-4,4a-dihydropyrano-[3,2-d][1,3]dioxin-6(8aH)-one

Guidance literature:

With dihydrogen peroxide;

DOI:10.1039/c39800000066

Reference yield:

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + [2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde (81577-69-7) → methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate + methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate (653565-47-0)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 23h; Overall yield = 92.8 %; Overall yield = 1.18 g; Inert atmosphere;

DOI:10.1021/acs.joc.6b02518

upstream raw materials:

trimethyl phosphonoacetate

[2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

(2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate