Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 306747-67-1
• Molecular Formula: C₂₈H₄₀O₁₃
• Molecular Weight: 584.618

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

There total 24 articles about Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-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:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester (306747-67-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 83 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 92 percent / mCPBA / CH₂Cl₂ / 2 h / -20 - 0 °C

4.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

5.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

6.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

7.1: 0.44 g / diethyl ether / 1 h / -78 °C

8.1: 97 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h / 25 °C

9.1: 87 percent / pyridine / 12 h / 0 - 25 °C

10.1: 86 percent / LiI / dimethylformamide / 2 h / 80 - 100 °C

11.1: 97 percent / nBu₃SnH; AIBN / benzene / 0.5 h / Heating

12.1: nBu₂SnO / toluene / 5 h / Heating

12.2: 63 percent / Bu₄NI / toluene / 8 h / Heating

13.1: TBAF / tetrahydrofuran / 6 h / 25 °C

14.1: 0.106 g / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Oxidation / 4.1: Glycosidation / 5.1: Oxidation / 6.1: Oxidation / 7.1: Methylation / 8.1: Hydrogenolysis / 9.1: Tosylation / 10.1: Substitution / 11.1: Reduction / 12.1: Cyclization / 12.2: Ring cleavage / 13.1: Silyl ether cleavage / 14.1: Acetylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7) → Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester (306747-67-1)

Guidance literature:

Multi-step reaction with 20 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 87 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

3.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

4.1: 97 percent / pyridine / 12 h / 0 - 25 °C

5.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

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

6.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NBS; H₂O / acetone / 2 h / 0 - 25 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

9.1: 98 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

11.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

12.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

13.1: 0.44 g / diethyl ether / 1 h / -78 °C

14.1: 97 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h / 25 °C

15.1: 87 percent / pyridine / 12 h / 0 - 25 °C

16.1: 86 percent / LiI / dimethylformamide / 2 h / 80 - 100 °C

17.1: 97 percent / nBu₃SnH; AIBN / benzene / 0.5 h / Heating

18.1: nBu₂SnO / toluene / 5 h / Heating

18.2: 63 percent / Bu₄NI / toluene / 8 h / Heating

19.1: TBAF / tetrahydrofuran / 6 h / 25 °C

20.1: 0.106 g / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; tri-n-butyl-tin hydride; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Reduction / 6.1: Metallation / 6.2: Methylation / 7.1: Hydrolysis / 8.1: Etherification / 9.1: Hydrolysis / 10.1: Glycosidation / 11.1: Oxidation / 12.1: Oxidation / 13.1: Methylation / 14.1: Hydrogenolysis / 15.1: Tosylation / 16.1: Substitution / 17.1: Reduction / 18.1: Cyclization / 18.2: Ring cleavage / 19.1: Silyl ether cleavage / 20.1: Acetylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9) → Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester (306747-67-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

2.1: 92 percent / mCPBA / CH₂Cl₂ / 2 h / -20 - 0 °C

3.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

5.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

6.1: 0.44 g / diethyl ether / 1 h / -78 °C

7.1: 97 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h / 25 °C

8.1: 87 percent / pyridine / 12 h / 0 - 25 °C

9.1: 86 percent / LiI / dimethylformamide / 2 h / 80 - 100 °C

10.1: 97 percent / nBu₃SnH; AIBN / benzene / 0.5 h / Heating

11.1: nBu₂SnO / toluene / 5 h / Heating

11.2: 63 percent / Bu₄NI / toluene / 8 h / Heating

12.1: TBAF / tetrahydrofuran / 6 h / 25 °C

13.1: 0.106 g / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 1.1: Etherification / 2.1: Oxidation / 3.1: Glycosidation / 4.1: Oxidation / 5.1: Oxidation / 6.1: Methylation / 7.1: Hydrogenolysis / 8.1: Tosylation / 9.1: Substitution / 10.1: Reduction / 11.1: Cyclization / 11.2: Ring cleavage / 12.1: Silyl ether cleavage / 13.1: Acetylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

upstream raw materials:

acetic anhydride

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 306747-67-1 Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send