methyl 5β,6α-dibenzyloxypolyangioate

Base Information

• Chemical Name: methyl 5β,6α-dibenzyloxypolyangioate
• CAS No.: 130799-17-6
• Molecular Formula: C₄₃H₅₆O₆
• Molecular Weight: 668.914
• Mol file: 130799-17-6.mol

Synonyms:methyl 5β,6α-dibenzyloxypolyangioate

Chemical Property of methyl 5β,6α-dibenzyloxypolyangioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 5β,6α-dibenzyloxypolyangioate

There total 49 articles about methyl 5β,6α-dibenzyloxypolyangioate 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:

(E)-(S)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-2-(toluene-4-sulfonyl)-hex-4-enoic acid methyl ester (130799-15-4) → methyl 5β,6α-dibenzyloxypolyangioate (130799-17-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / (Me)4NOAc / hexamethylphosphoric acid triamide / 17 h / 96 - 100 °C

2: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min

3: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C

With n-butyllithium; sodium amalgam; tetramethyl ammonium acetate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane;

DOI:10.1016/S0040-4020(01)88025-X

Reference yield:

(E)-3-methyl-1,3-hexadiene (105247-06-1) → methyl 5β,6α-dibenzyloxypolyangioate (130799-17-6)

Guidance literature:

Multi-step reaction with 9 steps

1: hydroquinone / CHCl₃ / 12 h / 120 °C

3: 1.) (COCl)2, DMF, 2.) PhCH₂PdCl(PPh₃)2 / 1.) CH₂Cl₂, 0 deg C - 20 deg C, 2 h, 2.) HMPA, 70 deg C, 3 h

4: 92 percent / tetrahydrofuran / 2 h / 0 °C

6: 92 percent / diethyl ether / Ambient temperature

7: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to RT, 24 h

8: 71 percent / Me₄NOAc / hexamethylphosphoric acid triamide / 17 h / 100 °C

With oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); tetramethyl ammonium acetate; N,N-dimethyl-formamide; hydroquinone; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; chloroform;

Reference yield:

(E)-1-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-but-2-en-1-one (130799-11-0) → methyl 5β,6α-dibenzyloxypolyangioate (130799-17-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / tetrahydrofuran / 2 h / 0 °C

3: 92 percent / diethyl ether / Ambient temperature

4: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to RT, 24 h

5: 71 percent / Me₄NOAc / hexamethylphosphoric acid triamide / 17 h / 100 °C

With tetramethyl ammonium acetate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether;

upstream raw materials:

(2R,6R)-2-[(E)-(S)-1,3-Dimethyl-4-(toluene-4-sulfonyl)-but-1-enyl]-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

5-(((S,E)-4-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-2-methylpent-3-en-1-yl)sulfonyl)-1-phenyl-1H-tetrazole

(R)-3-hydroxy-2-methylpent-1-ene

Downstream raw materials:

(+)-ambruticin S

5β,6α-dibenzyloxypolyangioic acid