4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 214483-53-1
• Molecular Formula: C₄₄H₅₀Cl₂O₁₁
• Molecular Weight: 825.78
• Mol file: 214483-53-1.mol

Synonyms:4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester

There total 39 articles about 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester 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-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoyl fluoride (214483-50-8) + (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-Benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol (214483-52-0) → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester (214483-53-1)

Guidance literature:

With n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; hexane; 1.) 25 deg C, 1 h, 2.) 24 h;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1874::AID-ANIE1874>3.0.CO;2-K

Reference yield:

(2R,3S)-3-((tert-butyldimethylsilyl)oxy)pent-4-en-2-ol (214483-57-5) → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester (214483-53-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 0.25 h / 0 °C

2.1: 90 percent / Grubbs' catalyst / CH₂Cl₂ / 34 h / 35 °C

3.1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

4.1: 90 percent / NMO; OsO₄; H₂O / acetone / 12 h / 25 °C

5.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

6.1: 69 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

7.1: 97 percent / K₂CO₃; MeOH / diethyl ether / 1 h / 25 °C

8.1: nBu₂SnO / toluene / 3 h / Heating

8.2: 92 percent / nBu₄NI / toluene / 2 h / Heating

9.1: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

10.1: SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 12 h / -10 °C

11.1: Raney Ni / methanol / 2 h / Heating

11.2: NaH / dimethylformamide / 0.08 h / 0 °C

11.3: nBu₄NI / dimethylformamide / 1 h / 0 - 25 °C

12.1: 0.11 g / TBAF / tetrahydrofuran / 1 h / 25 °C

13.1: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran; hexane / 1 h / 25 °C

13.2: 80 percent / tetrahydrofuran; hexane / 24 h

With methanol; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; nickel; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; 1.1: Esterification / 2.1: Cyclization / 3.1: Reduction / 4.1: Addition / 5.1: Acetylation / 6.1: Substitution / 7.1: Deacetylation / 8.1: Cyclization / 8.2: Ring cleavage / 9.1: Rearrangement / 10.1: Glycosidation / 11.1: Reduction / 11.2: Metallation / 11.3: Etherification / 12.1: Silyl ether cleavage / 13.1: Metallation / 13.2: Esterification;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

Acrylic acid (1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl ester (214483-36-0) → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl ester (214483-53-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 90 percent / Grubbs' catalyst / CH₂Cl₂ / 34 h / 35 °C

2.1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

3.1: 90 percent / NMO; OsO₄; H₂O / acetone / 12 h / 25 °C

4.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

5.1: 69 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

6.1: 97 percent / K₂CO₃; MeOH / diethyl ether / 1 h / 25 °C

7.1: nBu₂SnO / toluene / 3 h / Heating

7.2: 92 percent / nBu₄NI / toluene / 2 h / Heating

8.1: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

9.1: SnCl₂; molecular sieves 4 Angstroem / diethyl ether / 12 h / -10 °C

10.1: Raney Ni / methanol / 2 h / Heating

10.2: NaH / dimethylformamide / 0.08 h / 0 °C

10.3: nBu₄NI / dimethylformamide / 1 h / 0 - 25 °C

11.1: 0.11 g / TBAF / tetrahydrofuran / 1 h / 25 °C

12.1: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran; hexane / 1 h / 25 °C

12.2: 80 percent / tetrahydrofuran; hexane / 24 h

With methanol; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; nickel; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; 1.1: Cyclization / 2.1: Reduction / 3.1: Addition / 4.1: Acetylation / 5.1: Substitution / 6.1: Deacetylation / 7.1: Cyclization / 7.2: Ring cleavage / 8.1: Rearrangement / 9.1: Glycosidation / 10.1: Reduction / 10.2: Metallation / 10.3: Etherification / 11.1: Silyl ether cleavage / 12.1: Metallation / 12.2: Esterification;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

upstream raw materials:

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoyl fluoride

(2R,3R,4R,6S)-6-((2R,3R,4R,6R)-4-Benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-ol

2,4-dihydroxy-6-methylbenzaldehyde

methyl orsellinate

Downstream raw materials:

C₄₄H₅₅Cl₂NO₁₄

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3S,4R,6S)-6-((2R,3R,4R,6R)-4-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester