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

Base Information

Chemical Name:tert-Butyl-[(2R,3R,4S,5R)-6-fluoro-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane
CAS No.:306768-22-9
Molecular Formula:C₂₆H₃₇FO₄SSi
Molecular Weight:492.727
Hs Code.:

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

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

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

There total 12 articles about tert-Butyl-[(2R,3R,4S,5R)-6-fluoro-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-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: 100.0%

: 214483-45-1
(2R,3S,4R,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

: 306768-22-9
tert-Butyl-[(2R,3R,4S,5R)-6-fluoro-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at 0 ℃;
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

: 306768-22-9
tert-Butyl-[(2R,3R,4S,5R)-6-fluoro-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 10 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

With methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; lithium triethylborohydride; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 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;
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

: 306768-22-9
tert-Butyl-[(2R,3R,4S,5R)-6-fluoro-4-(4-methoxy-benzyloxy)-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 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

With methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 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;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4