(2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid

Base Information

• Chemical Name: (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid
• CAS No.: 632339-28-7
• Molecular Formula: C₂₄H₃₄O₅Si
• Molecular Weight: 430.616
• Mol file: 632339-28-7.mol

Synonyms:

Chemical Property of (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid

There total 7 articles about (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid 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: 25.0%

(2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3,5-dihydroxy-2-methyl-heptan-1-one (632339-27-6) → (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid (632339-28-7)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1055/s-2003-40856

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid (632339-28-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / D-(-)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

2: 90 percent / Red-Al / diethyl ether / -20 °C

3: 95 percent / PPTS / 25 °C

4: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

5: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

6: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

7: 95 percent / Dowex / methanol; H₂O / Heating

8: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

9: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium hydroxide; dowex; diethyl (2S,3S)-tartrate; di-n-butylboryl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → (2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2-methyl-heptanoic acid (632339-28-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / Red-Al / diethyl ether / -20 °C

2: 95 percent / PPTS / 25 °C

3: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

4: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

5: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

6: 95 percent / Dowex / methanol; H₂O / Heating

7: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

8: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

With 1H-imidazole; dmap; lithium hydroxide; dowex; di-n-butylboryl trifluoromethanesulfonate; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 4: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

upstream raw materials:

(2R,3S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3,5-dihydroxy-2-methyl-heptan-1-one

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

(E)-5-(benzyloxy)pent-2-en-1-ol

(S)-5-phenylmethoxypentane-1,3-diol

Downstream raw materials:

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-prop-2-en-1-ol

2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester

2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-ol