[(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

Base Information

• Chemical Name: [(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
• CAS No.: 854749-32-9
• Molecular Formula: C₃₈H₅₀O₇
• Molecular Weight: 618.811
• Mol file: 854749-32-9.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 18 articles about [(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 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:

(2R,3R)-2-((benzyloxy)methoxy)hex-5-en-3-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 (854749-32-9)

Guidance literature:

Multi-step reaction with 15 steps

1: KH / tetrahydrofuran

2: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

3: MgBr₂*Et₂O

4: 97 percent / imidazole / dimethylformamide

5: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

6: 92 percent / indium / dimethylformamide

7: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

8: O₃

9: 92 percent / NaH

10: HF*pyridine

11: camphorsulfonic acid / benzene / Heating

12: 84 percent / DIBAL-H / -78 °C

13: 66 percent / trimethylsilyl triflate / diethyl ether / -78 °C

14: tetrabutylammonium fluoride

15: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide

With 1H-imidazole; indium; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; ozone; 4-methylmorpholine N-oxide; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 9: Horner-Emmons reaction;

DOI:10.1021/ol050511w

Reference yield:

1-[(R)-1-((R)-1-Benzyloxymethoxy-ethyl)-but-3-enyloxymethyl]-4-methoxy-benzene → [(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 (854749-32-9)

Guidance literature:

Multi-step reaction with 14 steps

1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2: MgBr₂*Et₂O

3: 97 percent / imidazole / dimethylformamide

4: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

5: 92 percent / indium / dimethylformamide

6: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

7: O₃

8: 92 percent / NaH

9: HF*pyridine

10: camphorsulfonic acid / benzene / Heating

11: 84 percent / DIBAL-H / -78 °C

12: 66 percent / trimethylsilyl triflate / diethyl ether / -78 °C

13: tetrabutylammonium fluoride

14: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide

With 1H-imidazole; indium; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; ozone; 4-methylmorpholine N-oxide; pyridinium chlorochromate; magnesium bromide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 8: Horner-Emmons reaction;

DOI:10.1021/ol050511w

Reference yield:

(4S,6R,7R)-7-Benzyloxymethoxy-6-(4-methoxy-benzyloxy)-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 (854749-32-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / imidazole / dimethylformamide

2: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

3: 92 percent / indium / dimethylformamide

4: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

5: O₃

6: 92 percent / NaH

7: HF*pyridine

8: camphorsulfonic acid / benzene / Heating

9: 84 percent / DIBAL-H / -78 °C

10: 66 percent / trimethylsilyl triflate / diethyl ether / -78 °C

11: tetrabutylammonium fluoride

12: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide

With 1H-imidazole; indium; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 6: Horner-Emmons reaction;

DOI:10.1021/ol050511w

upstream raw materials:

{1-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal

(5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enethioic acid S-ethyl ester

Downstream raw materials:

C₄₀H₅₆O₁₀

(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

6-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-2-[3-(6-{6-[4-hydroxy-2-(4-methoxy-benzyloxy)-butyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-4-methylene-tetrahydro-pyran-2-yl)-1,1-dimethyl-allyl]-2-methoxy-tetrahydro-pyran-3-ol

C₇₁H₉₂O₁₀Si