[(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 214483-51-9
• Molecular Formula: C₄₆H₆₀O₈S₂Si
• Molecular Weight: 833.195
• Mol file: 214483-51-9.mol

Synonyms:[(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

There total 17 articles about [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 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,3S)-3-((tert-butyldimethylsilyl)oxy)pent-4-en-2-ol (214483-57-5) → [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (214483-51-9)

Guidance literature:

Multi-step reaction with 10 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

With methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; water; 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 diethyl ether; 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;

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) → [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (214483-51-9)

Guidance literature:

Multi-step reaction with 9 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

With methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; water; 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 diethyl ether; 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;

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) → [(2R,3R,4S,5R,6S)-6-((2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (214483-51-9)

Guidance literature:

Multi-step reaction with 11 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

With methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; lithium triethylborohydride; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; 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;

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

upstream raw materials:

(2R,3S)-3-((tert-butyldimethylsilyl)oxy)pent-4-en-2-ol

tert-Butyl-dimethyl-((S)-(R)-1-oxiranyl-allyloxy)-silane

Acrylic acid (1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl ester

(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-pyran-2-one

Downstream raw materials:

C₄₄H₅₅Cl₂NO₁₄

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

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

(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