{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Base Information

Chemical Name:{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester
CAS No.:189825-44-3
Molecular Formula:C₃₇H₆₁NO₁₃Si
Molecular Weight:755.976
Hs Code.:

{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Synonyms:{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

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Chemical Property of {(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

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Technology Process of {(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

There total 12 articles about {(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester 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:

: 58479-62-2
(2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol

: 189825-44-3
{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: (i-Pr)2NEt, Bu₄N⁽¹⁺⁾I^(1-) / CH₂Cl₂ / 20 h / Ambient temperature

2: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 25 °C

3: 1.) DMSO, trifluoroacetic anhydride, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, -78 deg C --> rt, 10 min, rt, 20 min

4: 1.) potassium bis(trimethylsilyl)amide / 1) THF, toluene, rt, 1 h; 2) THF, toluene, -78 deg C, 30 min, rt, 18 h

5: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, reflux, 6 h; 2) THF, DMF, rt, 18 h

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja9642929

Reference yield:

: 130669-74-8
(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

: 189825-44-3
{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / LiCl / tetrahydrofuran; nitromethane / 96 h / Ambient temperature

2: 76 percent / NaN₃ / dimethylformamide / 40 h / 55 °C

3: 99 percent / imidazole / dimethylformamide / 18 h / 60 °C

4: 1.) Ph₃P, 2.) H₂O / 1) THF, rt, 2 h; 2) THF, reflux, 6 h

5: aq. NaHCO₃ / ethyl acetate / 16 h / Ambient temperature

6: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, reflux, 6 h; 2) THF, DMF, rt, 18 h

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; water; sodium hydrogencarbonate; triphenylphosphine; lithium chloride; In tetrahydrofuran; nitromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja9642929

Reference yield:

: 189825-32-9
(1S,2S,5S,6S)-4-bromo-2-chloro-5,6-(O-isopropylidenedioxy)cyclohex-3-en-1-ol

: 189825-44-3
{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / NaN₃ / dimethylformamide / 40 h / 55 °C

2: 99 percent / imidazole / dimethylformamide / 18 h / 60 °C

3: 1.) Ph₃P, 2.) H₂O / 1) THF, rt, 2 h; 2) THF, reflux, 6 h

4: aq. NaHCO₃ / ethyl acetate / 16 h / Ambient temperature

5: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, reflux, 6 h; 2) THF, DMF, rt, 18 h

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; water; sodium hydrogencarbonate; triphenylphosphine; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja9642929