(S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal

Base Information

• Chemical Name: (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal
• CAS No.: 374900-93-3
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.505
• Mol file: 374900-93-3.mol

Synonyms:

Chemical Property of (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal

There total 7 articles about (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal 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:

(R)-(5'Z)-triisopropyl{2-[5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl]allyloxy}silane (337971-14-9) → (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal (374900-93-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 9-BBN / tetrahydrofuran

1.2: 66 percent / 30 percent H₂O₂; NaOH / tetrahydrofuran

2.1: 97 percent / n-Bu₃P

3.1: oxone / H₂O

4.1: n-BuLi / hexamethylphosphoric acid triamide

5.1: Na(Hg); Na₂HPO₄*12H₂O

6.1: n-Bu₄NF / tetrahydrofuran

7.1: (COCl)2; DMSO

With Oxone; disodium hydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; sodium amalgam; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; 7.1: Swern oxidation;

DOI:10.1246/cl.2001.898

Reference yield:

(R)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-3-triisopropylsilanyloxy-propan-1-ol (374900-89-7) → (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal (374900-93-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / n-Bu₃P

2: oxone / H₂O

3: n-BuLi / hexamethylphosphoric acid triamide

4: Na(Hg); Na₂HPO₄*12H₂O

5: n-Bu₄NF / tetrahydrofuran

6: (COCl)2; DMSO

With Oxone; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; 6: Swern oxidation;

DOI:10.1246/cl.2001.898

Reference yield:

Triisopropyl-((R)-2-{(R)-5-[2-(4-methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enyloxy)-silane (374900-92-2) → (S)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enal (374900-93-3)

Guidance literature:

Multi-step reaction with 2 steps

1: n-Bu₄NF / tetrahydrofuran

2: (COCl)2; DMSO

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; 2: Swern oxidation;

DOI:10.1246/cl.2001.898

upstream raw materials:

(R)-(5'Z)-triisopropyl{2-[5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl]allyloxy}silane

(R)-2-{(R)-5-[2-(4-Methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-3-triisopropylsilanyloxy-propan-1-ol

Triisopropyl-((R)-2-{(R)-5-[2-(4-methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-6-methyl-hept-5-enyloxy)-silane

Triisopropyl-((R)-2-{(R)-5-[2-(4-methoxy-benzyloxy)-eth-(Z)-ylidene]-tetrahydro-pyran-2-yl}-3-phenylsulfanyl-propoxy)-silane