(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane
CAS No.:746641-45-2
Molecular Formula:C₂₇H₄₆O₄Si
Molecular Weight:462.745
Hs Code.:

Synonyms:(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

There total 9 articles about (4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 746641-43-0
(αR,4S,5R)-5-[(benzyloxy)methyl]-α-[(2E)-1,1-dimethylbut-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-ethanol

: 746641-45-2
(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 2h;
DOI:10.1002/hlca.200490111

Reference yield:

: 28697-53-2
D-arabinopyranose

: 746641-45-2
(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / acetyl chloride / 24 h / 50 °C

2: 16.2 g / TsOH / acetone / 40 h

3: 81 percent / N-hydroxysuccinimide / pyridine; acetonitrile / 6 h / 20 °C

4: 65 percent / tributylstannane; azobis[isobutyronitrile] / toluene / 10 h / 80 °C

5: 100 percent / H₂ / Pd(OH)2 / tetrahydrofuran / 12 h

6: 67 percent / pyridin-2-ol / CH₂Cl₂ / 168 h / 20 °C / 6.00048e+06 - 6.75054e+06

7: 76 percent / NaH / dimethylformamide; tetrahydrofuran / 10 h

8: 93 percent / 2,6-lutidine / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; 2-hydroxypyridin; 1-hydroxy-pyrrolidine-2,5-dione; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetyl chloride; palladium dihydroxide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1002/hlca.200490111

Reference yield:

: 746641-41-8
benzyl 2-deoxy-3,4-O-isopropylidene-D-erythro-pentopyranoside

: 746641-45-2
(4R,5S)-4-[(benzyloxy)methyl]-5-{(2R,4E)-2-{[(tert-butyl)dimethylsilyl]oxy}-3,3-dimethylhex-4-en-yl}-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd(OH)2 / tetrahydrofuran / 12 h

2: 67 percent / pyridin-2-ol / CH₂Cl₂ / 168 h / 20 °C / 6.00048e+06 - 6.75054e+06

3: 76 percent / NaH / dimethylformamide; tetrahydrofuran / 10 h

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 2 h

With 2,6-dimethylpyridine; 2-hydroxypyridin; hydrogen; sodium hydride; palladium dihydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200490111