Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester

Base Information

• Chemical Name: Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester
• CAS No.: 915314-94-2
• Molecular Formula: C₂₅H₃₂NO₆P
• Molecular Weight: 473.506
• Mol file: 915314-94-2.mol

Synonyms:Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester

Chemical Property of Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester

There total 4 articles about Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester 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:

(4S,7S)-4,7-Bis-benzyloxymethyl-2-methoxy-4,7-dihydro-[1,3,2]dioxaphosphepine 2-oxide (915314-86-2) + 3-cyanopropylzinc bromide (135579-85-0) → Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester (915314-94-2)

Guidance literature:

3-cyanopropylzinc bromide; With CuCN*2LiCl; In tetrahydrofuran; at -30 - -25 ℃; for 1h;

(4S,7S)-4,7-Bis-benzyloxymethyl-2-methoxy-4,7-dihydro-[1,3,2]dioxaphosphepine 2-oxide; In tetrahydrofuran; for 2h;

DOI:10.1021/ol061756r

Reference yield:

bis((S)-1-(benzyloxy)but-3-en-2-yl) methyl phosphate (915315-05-8) → Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester (915314-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / (IMesH₂)(PCy₃)Cl₂Ru=CHPh / toluene / 0.5 h / Heating

2.1: CuCN*2LiCl / tetrahydrofuran / 1 h / -30 - -25 °C

2.2: tetrahydrofuran / 2 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; toluene;

DOI:10.1021/ol061756r

Reference yield:

(S)-1-(benzyloxy)but-3-en-2-ol (109613-59-4) → Phosphoric acid (1S,2R)-1-benzyloxymethyl-2-((E)-3-benzyloxy-propenyl)-5-cyano-pentyl ester methyl ester (915314-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / BuLi / tetrahydrofuran / -30 - 20 °C

2.1: 68 percent / (IMesH₂)(PCy₃)Cl₂Ru=CHPh / toluene / 0.5 h / Heating

3.1: CuCN*2LiCl / tetrahydrofuran / 1 h / -30 - -25 °C

3.2: tetrahydrofuran / 2 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; In tetrahydrofuran; toluene;

DOI:10.1021/ol061756r

upstream raw materials:

(4S,7S)-4,7-Bis-benzyloxymethyl-2-methoxy-4,7-dihydro-[1,3,2]dioxaphosphepine 2-oxide

3-cyanopropylzinc bromide

bis((S)-1-(benzyloxy)but-3-en-2-yl) methyl phosphate

(S)-1-(benzyloxy)but-3-en-2-ol