(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol
CAS No.:107108-72-5
Molecular Formula:C₂₀H₃₂O₅SSi
Molecular Weight:412.623
Hs Code.:

Synonyms:(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

There total 9 articles about (2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-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: 95.0%

: 107108-71-4
{(Z)-2-[(2R,3S,6R)-6-tert-Butoxy-3-(1-methoxy-1-methyl-ethoxy)-tetrahydro-pyran-2-yl]-1-phenylsulfanyl-vinyl}-trimethyl-silane

: 107108-72-5
(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 0 deg C, 1.5 h; room temp., 20 min;
DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

: 69247-20-7,149279-18-5,23339-25-5
tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

: 107108-72-5
(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

2: Et₃N, H₂O / methanol / Ambient temperature

3: CH₂Cl₂ / 0 deg C, then room temp., overnight

4: 86 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 93 percent / KOH, H₂O / methanol / 1.75 h

6: 78 percent / dipyridinium chromate / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 30 percent / n-BuLi / methanol / -45 °C

8: 95 percent / MCPBA, aq.NaHCO₃(sat) / CH₂Cl₂ / 0 deg C, 1.5 h; room temp., 20 min

With potassium hydroxide; n-butyllithium; pyridinium dichromate; camphor-10-sulfonic acid; water; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

: 2873-29-2
D-glucal triacetate

: 107108-72-5
(2R,3S,6R)-2-((Z)-2-Benzenesulfonyl-2-trimethylsilanyl-vinyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / BF₃-Et₂O / 1.67 h / Ambient temperature

2: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

3: Et₃N, H₂O / methanol / Ambient temperature

4: CH₂Cl₂ / 0 deg C, then room temp., overnight

5: 86 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 93 percent / KOH, H₂O / methanol / 1.75 h

7: 78 percent / dipyridinium chromate / CH₂Cl₂ / 0.17 h / Ambient temperature

8: 30 percent / n-BuLi / methanol / -45 °C

9: 95 percent / MCPBA, aq.NaHCO₃(sat) / CH₂Cl₂ / 0 deg C, 1.5 h; room temp., 20 min

With potassium hydroxide; n-butyllithium; pyridinium dichromate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; water; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(01)90575-7