Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester
CAS No.:306768-21-8
Molecular Formula:C₂₂H₃₄O₆SSi
Molecular Weight:454.66
Hs Code.:

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-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: 69.0%

: 108-98-5
thiophenol

: 214483-39-3
Acetic acid (3S,4R,5R,6R)-2,3-diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

: 306768-21-8
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 25 ℃; for 3h;
DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1874::AID-ANIE1874>3.0.CO;2-K

Reference yield:

: 214483-35-9
tert-Butyl-dimethyl-((S)-(R)-1-oxiranyl-allyloxy)-silane

: 306768-21-8
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 0.25 h / 0 °C

3: 90 percent / Grubbs' catalyst / CH₂Cl₂ / 34 h / 35 °C

4: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

5: 90 percent / NMO; OsO₄; H₂O / acetone / 12 h / 25 °C

6: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

7: 69 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; lithium triethylborohydride; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; acetone; 1: Reduction / 2: Esterification / 3: Cyclization / 4: Reduction / 5: Addition / 6: Acetylation / 7: Substitution;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

: 214483-36-0
Acrylic acid (1R,2S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-but-3-enyl ester

: 306768-21-8
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / Grubbs' catalyst / CH₂Cl₂ / 34 h / 35 °C

2: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

3: 90 percent / NMO; OsO₄; H₂O / acetone / 12 h / 25 °C

4: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

5: 69 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; triethylamine; Grubbs catalyst first generation; In dichloromethane; acetone; 1: Cyclization / 2: Reduction / 3: Addition / 4: Acetylation / 5: Substitution;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4