(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

Base Information

Chemical Name:(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane
CAS No.:203515-77-9
Molecular Formula:C₄₃H₈₀O₈Si₃
Molecular Weight:809.36
Hs Code.:

(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

Synonyms:(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

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Chemical Property of (1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

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Purity/Quality:

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Technology Process of (1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

There total 25 articles about (1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane 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:

: 203515-76-8
(2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(S)-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-yl] (triethylsiloxy)methyl] tetrahydro-6-methoxy-3-methyl-2-(4-benzyloxybutyl)-2H-pyran

: 203515-77-9
(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 ℃; Yield given;
DOI:10.1002/anie.199727411

Reference yield:

: 994-30-9
triethylsilyl chloride

: 203515-77-9
(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 13 steps

1: imidazole

2: DIBALH / -78 °C

3: 81 percent / POCl₃, pyridine / 80 °C

4: 99 percent / LDBB / tetrahydrofuran / -78 °C

5: 1.) SO₃*pyridine, DMSO, 2.) Et₃N

6: NaClO₂, 2-methyl-2-butene, ethyl-1-propenyl ether / 2-methyl-propan-2-ol / pH 5.5

7: 1-chloro-N,N-trimethylpropenylamine

8: pyridine, DMAP

9: LDA / tetrahydrofuran / -78 °C

10: 1.) ZnI₂, 2.) MgBr₂*Et₂O / 1.) r.t., 2.) reflux

11: 90 percent / KBHEt₃ / tetrahydrofuran / -78 - -40 °C

12: 97 percent / imidazole / dimethylformamide

13: dimethyldioxirane / acetone; CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; 2-methyl-but-2-ene; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; ethyl-1-propenyl ether; 3,3-dimethyldioxirane; diisobutylaluminium hydride; potassium triethylborohydride; dimethyl sulfoxide; triethylamine; zinc(II) iodide; magnesium bromide; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1002/anie.199727411

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 203515-77-9
(1R,3R,4S,5R,6S)-3-{(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-triethylsilanyloxy-methyl}-4-methyl-5-triethylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 10 steps

1: imidazole / dimethylformamide

2: 1.) 9-BBN, 2.) H₂O₂

3: ZnI₂

4: NaH, Bu₄NI

5: 97 percent / m-CPBA, NaHCO₃

6: LDA / tetrahydrofuran / -78 °C

7: 1.) ZnI₂, 2.) MgBr₂*Et₂O / 1.) r.t., 2.) reflux

8: 90 percent / KBHEt₃ / tetrahydrofuran / -78 - -40 °C

9: 97 percent / imidazole / dimethylformamide

10: dimethyldioxirane / acetone; CH₂Cl₂ / 0 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium triethylborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/anie.199727411