(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol
CAS No.:214483-41-7
Molecular Formula:C₂₅H₃₆O₄SSi
Molecular Weight:460.71
Hs Code.:

Synonyms:(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 13 articles about (2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 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%

: 100-39-0
benzyl bromide

: 824-94-2
p-methoxybenzyl chloride

: 214483-40-6
(2R,3S,4R,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol

: 214483-41-7
(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: (2R,3S,4R,5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

benzyl bromide; p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; In toluene; for 2h; Heating;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

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

: 214483-41-7
(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 9 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: 80 percent / nBu₄NI / toluene / 2 h / Heating

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; 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;
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

: 214483-41-7
(2R,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 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: 80 percent / nBu₄NI / toluene / 2 h / Heating

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