2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl ester
• CAS No.: 134004-77-6
• Molecular Formula: C₄₉H₆₉O₇PSi
• Molecular Weight: 829.142

Synonyms:2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl ester

Chemical Property of 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl ester

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Technology Process of 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl ester

There total 2 articles about 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ⁵-phospha-tricyclo[7.4.0.0^1,5]tridec-8-yl 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:

6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (134004-76-5) + dichlorotriphenylphosphorane (2526-64-9) → 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ5-phospha-tricyclo[7.4.0.01,5]tridec-8-yl ester (134004-77-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In [D₃]acetonitrile; for 3.5h; Ambient temperature;

DOI:10.1021/jo00011a022

Reference yield:

6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one (127343-13-9) → 2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ5-phospha-tricyclo[7.4.0.01,5]tridec-8-yl ester (134004-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / H₂O, trimethylamine N-oxide dihydrate, pyridine, OsO₄ / acetone / 18 h / 60 - 62 °C

2: diisopropylethylamine / CD₃CN / 3.5 h / Ambient temperature

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; water; N-ethyl-N,N-diisopropylamine; In [D₃]acetonitrile; acetone;

DOI:10.1021/jo00011a022

Reference yield: 27.0%

2,2-Dimethyl-butyric acid (1R,5S,6R,8S,9S,10S,11S)-10-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-6,11-dimethyl-3,3,3-triphenyl-2,4-dioxa-3λ5-phospha-tricyclo[7.4.0.01,5]tridec-8-yl ester (134004-77-6) → 2,2-Dimethyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester (134004-70-9) + C49H68O6PSi(1+)*Cl(1-) (134028-79-8) + 6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5-oxo-1,2,3,4,5,6,7,8,8a(R)-nonahydronaphtyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one (127343-16-2)

Guidance literature:

for 16h;

DOI:10.1021/jo00011a022

upstream raw materials:

6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-4a(R),5(S)-dihydroxy-2(S),6(R)-dimethyl-1,2,3,4,4a,5,6,7,8,8a(R)-decahydronaphth-1(S)-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one

dichlorotriphenylphosphorane

6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-1,2,3,4,6,7,8,8a(R)-octahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one

Downstream raw materials:

2,2-Dimethyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester

C₄₉H₆₈O₆PSi⁽¹⁺⁾*Cl^(1-)

6(R)-<2-<8(S)-<(2,2-dimethylbutyryl)oxy>-2(S),6(R)-dimethyl-5-oxo-1,2,3,4,5,6,7,8,8a(R)-nonahydronaphtyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one

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