{(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester

Base Information

• Chemical Name: {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester
• CAS No.: 198469-47-5
• Molecular Formula: C₅₇H₇₂O₁₁Si
• Molecular Weight: 961.278
• Mol file: 198469-47-5.mol

Synonyms:{(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester

Chemical Property of {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester

There total 11 articles about {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl 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:

D-(-)-quinic acid (77-95-2) → {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester (198469-47-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / H⁺ / 16 h / Ambient temperature

2: 80 percent / methanol / 3 h / 0 °C

3: 95 percent / DMAP / 16 h / Ambient temperature

5: 80 percent / dimethylformamide / 16 h / Ambient temperature

6: 1.) H₂, 2.) LAH / 1.) Pd/C / 1.) rt, 1 h, 2.) rt

7: 86 percent / NaH / 1 h / Ambient temperature

8: 1.) O₃ / 1.) DMS, -78 deg C, 1 h, 2.) -78 deg C, 4 h

9: 82 percent / AgOTf / 0 °C

10: 86 percent / aq. AcOH / 2 h / 80 °C

11: 1.) Bu₂SnO / 1.) 100 deg C, 16 h, 2.) 100 deg C, 16 h

With dmap; lithium aluminium tetrahydride; hydrogen; silver trifluoromethanesulfonate; hydrogen cation; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10077-4

Reference yield:

3,4-isopropylidenequinide (130474-38-3) → {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester (198469-47-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / methanol / 3 h / 0 °C

2: 95 percent / DMAP / 16 h / Ambient temperature

4: 80 percent / dimethylformamide / 16 h / Ambient temperature

5: 1.) H₂, 2.) LAH / 1.) Pd/C / 1.) rt, 1 h, 2.) rt

6: 86 percent / NaH / 1 h / Ambient temperature

7: 1.) O₃ / 1.) DMS, -78 deg C, 1 h, 2.) -78 deg C, 4 h

8: 82 percent / AgOTf / 0 °C

9: 86 percent / aq. AcOH / 2 h / 80 °C

10: 1.) Bu₂SnO / 1.) 100 deg C, 16 h, 2.) 100 deg C, 16 h

With dmap; lithium aluminium tetrahydride; hydrogen; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10077-4

Reference yield:

methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate (97373-88-1) → {(1R,2R,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-5-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-cyclohexyloxy}-acetic acid methyl ester (198469-47-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / DMAP / 16 h / Ambient temperature

3: 80 percent / dimethylformamide / 16 h / Ambient temperature

4: 1.) H₂, 2.) LAH / 1.) Pd/C / 1.) rt, 1 h, 2.) rt

5: 86 percent / NaH / 1 h / Ambient temperature

6: 1.) O₃ / 1.) DMS, -78 deg C, 1 h, 2.) -78 deg C, 4 h

7: 82 percent / AgOTf / 0 °C

8: 86 percent / aq. AcOH / 2 h / 80 °C

9: 1.) Bu₂SnO / 1.) 100 deg C, 16 h, 2.) 100 deg C, 16 h

With dmap; lithium aluminium tetrahydride; hydrogen; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10077-4

upstream raw materials:

bromoacetic acid methyl ester

D-(-)-quinic acid

3,4-isopropylidenequinide

methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate