methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside
CAS No.:299410-80-3
Molecular Formula:C₂₂H₃₆O₇Si
Molecular Weight:440.609
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

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Chemical Property of methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

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Technology Process of methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

There total 1 articles about methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside 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: 93.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 299410-79-0
(2R,4aR,6S,7S,8S,8aR)-8-(2-Hydroxy-ethoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 299410-80-3
methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1021/ol006222j

Reference yield: 86.0%

: 299410-80-3
methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

: 299410-81-4
methyl 4-O-benzoyl-6-bromo-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-6-deoxy-α-D-altropyranoside

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 1h; Heating;
DOI:10.1021/jo0491051

Reference yield:

: 299410-80-3
methyl 4,6-O-benzylidene-3-O-[2-{(tert-butyldimethylsilyl)oxy}ethyl]-α-D-altropyranoside

: 2alpha-(3-hydroxypropoxy)-1alpha,25-dihydroxyvitamin D₃

Guidance literature:: Multi-step reaction with 11 steps

1.1: 71 percent / NBS; BaCO₃ / CCl₄ / 0.58 h / Heating

2.1: 95 percent / NaOMe / methanol

3.1: 93 percent / imidazole / dimethylformamide

4.1: Bu₄NF / tetrahydrofuran

5.1: Zn; NaBH₃CN / propan-1-ol; H₂O / 0.75 h / 95 °C

5.2: 71 percent / NaBH₄

6.1: TmCl; DMAP / CH₂Cl₂

6.2: LiHMDS / tetrahydrofuran / -78 - 20 °C

7.1: 91 percent / BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

8.1: 93 percent / K₂CO₃ / methanol

9.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10.1: 75 percent / Pd(PPh₃)4; Et₃N / toluene / Heating

11.1: 78 percent / Bu₄NF / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium cyanoborohydride; potassium carbonate; triethylamine; barium carbonate; zinc; In tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Bromination / 2.1: deacylation / 3.1: Substitution / 4.1: Substitution / 5.1: Ring cleavage / 5.2: Reduction / 6.1: Substitution / 6.2: Cyclization / 7.1: Ring cleavage / 8.1: Substitution / 9.1: Substitution / 10.1: Cyclization / 11.1: Substitution;
DOI:10.1021/ol006222j