(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

Base Information

Chemical Name:(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol
CAS No.:1289512-61-3
Molecular Formula:C₃₄H₆₀O₇Si₂
Molecular Weight:637.017
Hs Code.:

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

Synonyms:(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

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Chemical Property of (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

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Technology Process of (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

There total 1 articles about (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol 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: 45.0%

: 1063713-63-2
(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

: (S)-1-((2R,4R,5S)-5-((1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl)-4-hydroxy-5-methyltetrahydrofuran-2-yl)ethane-1,2-diol

: (2S,3R,5R)-2-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-5-{(S)-1-[(tert-butyldimethylsilyl)oxy]-2-hydroxyethyl}-5-methyltetrahydrofuran-3-ol

: 1289512-61-3
(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;
DOI:10.1002/ejoc.201001411

Reference yield: 93.0%

: 1289512-61-3
(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

: 1289512-63-5
(R)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]acetaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -50 - -30 ℃; for 0.133333h; Inert atmosphere;

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol; In dichloromethane; at -30 ℃; for 0.75h; Inert atmosphere;

With triethylamine; In dichloromethane; at -30 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1002/ejoc.201001411

Reference yield:

: 1289512-61-3
(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

: 1289512-98-6
((S)-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-((2R,5R,7S)-7((S)-1-[(tert-butyldiphenylsilyl)oxy]propan-2-yl)-1,6-dioxaspiro[4.5]decan-2-yl)methoxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

1.2: 0.75 h / -30 °C / Inert atmosphere

1.3: 0.17 h / -30 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 17 h / Inert atmosphere; Reflux

4.1: pyridine; 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 4 h / Inert atmosphere

5.1: chloroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; 5% Pd(II)/C(eggshell); hydrogen; dimethyl sulfoxide; chloroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: Swern oxidation / 1.2: Swern oxidation / 1.3: Swern oxidation;
DOI:10.1002/ejoc.201001411