(R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid

Base Information

• Chemical Name: (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid
• CAS No.: 854749-36-3
• Molecular Formula: C₄₀H₅₈O₁₁
• Molecular Weight: 714.894
• Mol file: 854749-36-3.mol

Synonyms:(R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid

Chemical Property of (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid

There total 12 articles about (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid 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: 80.0%

4-{6-[6-(3-{6-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-2-methoxy-3-oxo-tetrahydro-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-ylmethyl]-4-methylene-tetrahydro-pyran-2-yl}-3-(4-methoxy-benzyloxy)-butyric acid → (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid (854749-36-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1021/ol050512o

Reference yield:

(S)-5-((tert-butyldiphenylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal (854749-30-7) → (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid (854749-36-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / MgBr₂*Et₂O / -78 °C

2: 80 percent / trimethylsilyl triflate / diethyl ether / -78 °C

3: mCPBA

4: tetra-n-butylammonium fluoride

5: tetrapropylammonium perruthanate; N-methylmorpholine N-oxide

6: 80 percent / DDQ / H₂O; CH₂Cl₂

With tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; In diethyl ether; dichloromethane; water; 6: Pinnick oxidation;

DOI:10.1021/ol050512o

Reference yield:

(4S,6S)-8-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-trimethylsilanylmethyl-oct-1-en-4-ol (854749-31-8) → (R)-4-[(2S,6R)-6-((2S,6R)-6-{(E)-3-[(2S,6S)-6-((2R,3R)-3-Benzyloxymethoxy-2-hydroxy-butyl)-2-methoxy-3-oxo-tetrahydro-pyran-2-yl]-3-methyl-but-1-enyl}-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-methylene-tetrahydro-pyran-2-yl]-3-hydroxy-butyric acid (854749-36-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / trimethylsilyl triflate / diethyl ether / -78 °C

2: mCPBA

3: tetra-n-butylammonium fluoride

4: tetrapropylammonium perruthanate; N-methylmorpholine N-oxide

5: 80 percent / DDQ / H₂O; CH₂Cl₂

With tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; 5: Pinnick oxidation;

DOI:10.1021/ol050512o

upstream raw materials:

(S)-5-((tert-butyldiphenylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal

(4S,6S)-8-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-trimethylsilanylmethyl-oct-1-en-4-ol

[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-acetaldehyde

{2-[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane