(4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol

Base Information

• Chemical Name: (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol
• CAS No.: 921207-71-8
• Molecular Formula: C₂₅H₃₂O₄
• Molecular Weight: 396.527
• Mol file: 921207-71-8.mol

Synonyms:(4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol

Chemical Property of (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol

There total 14 articles about (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-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: 76.0%

5-{(2S,4S,6S)-6-[3-(benzyloxy)propyl]-2-phenyl-1,3-dioxan-4-yl}-1-penten-4-one (921207-70-7) → (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol (921207-71-8) + (4S)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -100 ℃; for 3h;

DOI:10.1021/ol062595u

Reference yield:

((hept-6-yn-1-yloxy)methyl)benzene (565473-04-3) → (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol (921207-71-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 93 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.1: Ph₃P; phenol / benzene / 12 h / 50 °C

2.2: 95 percent / MeI / diethyl ether / 12 h / Heating

3.1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / (DHQD)2-PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 0 °C

3.2: MeI / diethyl ether / 12 h / Heating

3.3: 27.9 g / pyridine; DMAP / CH₂Cl₂ / -78 - 0 °C

4.1: 90 percent / PPh₃; triethylamine; HCOOH / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 20 °C

5.1: 59 percent / t-BuOK / tetrahydrofuran / 0 °C

6.1: 89 percent / isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 0.5 h / cooling

7.1: 86 percent / tetrahydrofuran / 0.5 h / 0 °C

8.1: 76 percent / L-Selectride / tetrahydrofuran / 3 h / -100 °C

With n-butyllithium; formic acid; methanesulfonamide; potassium tert-butylate; isopropylmagnesium chloride; L-Selectride; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); phenol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; diethyl ether; hexane; water; tert-butyl alcohol; benzene; 2.1: Trost isomerization / 3.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ol062595u

Reference yield:

ethyl 8-benzyloxy-oct-2-ynoate (921207-66-1) → (4R)-5-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-en-4-ol (921207-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Ph₃P; phenol / benzene / 12 h / 50 °C

1.2: 95 percent / MeI / diethyl ether / 12 h / Heating

2.1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / (DHQD)2-PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 0 °C

2.2: MeI / diethyl ether / 12 h / Heating

2.3: 27.9 g / pyridine; DMAP / CH₂Cl₂ / -78 - 0 °C

3.1: 90 percent / PPh₃; triethylamine; HCOOH / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 20 °C

4.1: 59 percent / t-BuOK / tetrahydrofuran / 0 °C

5.1: 89 percent / isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 0.5 h / cooling

6.1: 86 percent / tetrahydrofuran / 0.5 h / 0 °C

7.1: 76 percent / L-Selectride / tetrahydrofuran / 3 h / -100 °C

With formic acid; methanesulfonamide; potassium tert-butylate; isopropylmagnesium chloride; L-Selectride; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); phenol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; diethyl ether; water; tert-butyl alcohol; benzene; 1.1: Trost isomerization / 2.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/ol062595u

upstream raw materials:

5-{(2S,4S,6S)-6-[3-(benzyloxy)propyl]-2-phenyl-1,3-dioxan-4-yl}-1-penten-4-one

2-[(2S,4S,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

(3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole

2-(2S,4R,6S)-6-[3-(benzyloxy)propyl]-2-phenyl-1,3-dioxan-4-yl-1-ethanol

Downstream raw materials:

(3S,5R,7R)-7-(benzyloxy)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

methyl 2-{(1E,4R)-4-benzyloxy-5-[(2S,4R,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-enyl}-6-methoxy-benzoate

(4R)-4-benzyloxy-5-[(2S,4R,6S)-6-(3-benzyloxy-propyl)-2-phenyl-1,3-dioxan-4-yl]pent-1-ene