(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

Base Information

Chemical Name:(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol
CAS No.:1289512-99-7
Molecular Formula:C₃₂H₄₈O₉
Molecular Weight:576.728
Hs Code.:

(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

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Chemical Property of (2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

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Technology Process of (2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

There total 11 articles about (2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-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:

: C₃₂H₄₈O₉

: 1289512-99-7
(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 19h; Inert atmosphere;
DOI:10.1002/ejoc.201001411

Reference yield:

: 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

: 1289512-99-7
(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

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

2.2: 0.75 h / -30 °C / Inert atmosphere

2.3: 0.17 h / -30 °C / Inert atmosphere

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

3.2: -78 - 20 °C / Inert atmosphere

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

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

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

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

8.1: toluene-4-sulfonic acid / dichloromethane / 19 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); tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; chloroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; 2.1: Swern oxidation / 2.2: Swern oxidation / 2.3: Swern oxidation;
DOI:10.1002/ejoc.201001411

Reference yield:

: 1289512-65-7
(1S,2R)-1-((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)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

: 1289512-99-7
(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

5: toluene-4-sulfonic acid / dichloromethane / 19 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 5% Pd(II)/C(eggshell); tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; chloroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201001411