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

Base Information

• Chemical Name: 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
• CAS No.: 214483-54-2
• Molecular Formula: C₃₆H₄₂Cl₂O₁₀
• Molecular Weight: 705.629
• Mol file: 214483-54-2.mol

Synonyms: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

Chemical Property of 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

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,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

There total 41 articles about 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 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-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) → 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 (214483-54-2)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 25 ℃; for 2h;

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

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,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 (214483-54-2)

Guidance literature:

Multi-step reaction with 13 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

13.1: 80 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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 / 13.1: Oxidation;

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

Reference yield:

tert-Butyl-dimethyl-((S)-(R)-1-oxiranyl-allyloxy)-silane (214483-35-9) → 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 (214483-54-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 91 percent / LiEt₃BH / tetrahydrofuran / 1 h / -40 °C

2.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 90 percent / Grubbs' catalyst / CH₂Cl₂ / 34 h / 35 °C

4.1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

5.1: 90 percent / NMO; OsO₄; H₂O / acetone / 12 h / 25 °C

6.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

7.1: 69 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

8.1: 97 percent / K₂CO₃; MeOH / diethyl ether / 1 h / 25 °C

9.1: nBu₂SnO / toluene / 3 h / Heating

9.2: 92 percent / nBu₄NI / toluene / 2 h / Heating

10.1: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

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

12.1: Raney Ni / methanol / 2 h / Heating

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

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

13.1: 0.11 g / TBAF / tetrahydrofuran / 1 h / 25 °C

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

14.2: 80 percent / tetrahydrofuran; hexane / 24 h

15.1: 80 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

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; lithium triethylborohydride; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; 1.1: Reduction / 2.1: Esterification / 3.1: Cyclization / 4.1: Reduction / 5.1: Addition / 6.1: Acetylation / 7.1: Substitution / 8.1: Deacetylation / 9.1: Cyclization / 9.2: Ring cleavage / 10.1: Rearrangement / 11.1: Glycosidation / 12.1: Reduction / 12.2: Metallation / 12.3: Etherification / 13.1: Silyl ether cleavage / 14.1: Metallation / 14.2: Esterification / 15.1: Oxidation;

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-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

2,4-dihydroxy-6-methylbenzaldehyde

methyl orsellinate

orsellinic acid

Downstream raw materials:

C₄₄H₅₅Cl₂NO₁₄