(2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol

Base Information

• Chemical Name: (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol
• CAS No.: 1240510-48-8
• Molecular Formula: C₃₄H₃₅BO₅
• Molecular Weight: 534.46
• Mol file: 1240510-48-8.mol

Synonyms:(2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol

Chemical Property of (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol

There total 2 articles about (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-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: 42.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (4'R,5'R,2E)-3-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]prop-2-en-1-yl methanesulfonate (1240510-17-1) → (2R,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol (1240510-39-7) + (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol (1240510-48-8)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; water; tin(ll) chloride; In N,N-dimethyl-formamide; at 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo1008959

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C39H47BO5Si → (2R,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol (1240510-39-7) + (2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol (1240510-48-8)

Guidance literature:

C₃₉H₄₇BO₅Si; With tetrahydroxydiboron; In dimethyl sulfoxide; acetonitrile; at 20 ℃;

formaldehyd; With tetrakis(acetonitrile)palladium(II) tetrafluoroborate; toluene-4-sulfonic acid; In dimethyl sulfoxide; acetonitrile; at 6 ℃; for 18h; Overall yield = 84 %; diastereoselective reaction;

DOI:10.1021/jo5004168

Reference yield: 95.0%

(2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol (1240510-48-8) + benzaldehyde (100-52-7) → (5R,2Z)-5-phenylpent-2-ene-1,5-diol (1240510-62-6)

Guidance literature:

(2S,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]but-3-en-1-ol; benzaldehyde; In dichloromethane; at 0 - 20 ℃; for 60h; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran; diethyl ether; at 0 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo1008959

upstream raw materials:

formaldehyd

(4'R,5'R,2E)-3-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]prop-2-en-1-yl methanesulfonate

Downstream raw materials:

(5S,2Z)-7-phenylhept-2-ene-1,5-diol

(5R,2Z)-5-phenylpent-2-ene-1,5-diol

(2Z,5R,6E)-7-(2-nitrophenyl)hepta-2,6-diene-1,5-diol

(2Z,5R,6E)-7-(4-nitrophenyl)hepta-2,6-diene-1,5-diol