(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

Base Information

Chemical Name:(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one
CAS No.:198469-41-9
Molecular Formula:C₅₆H₆₈O₁₁Si
Molecular Weight:945.235
Hs Code.:

(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

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Chemical Property of (4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

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Technology Process of (4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

There total 9 articles about (4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one 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:

: 77-95-2
D-(-)-quinic acid

: 198469-41-9
(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

Guidance literature:: Multi-step reaction with 10 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

4: 90 percent / NaBH₄ / ethanol / 3 h / Ambient temperature

5: 73 percent / NaH / 1 h / Ambient temperature

6: 90 percent / O₃ / various solvent(s) / 1 h / -78 °C

7: 78 percent / 4 h / -78 °C

8: 76 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; sodium tetrahydroborate; silver trifluoromethanesulfonate; hydrogen cation; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; In methanol; ethanol;
DOI:10.1016/S0960-894X(97)10077-4

Reference yield:

: 130474-38-3
3,4-isopropylidenequinide

: 198469-41-9
(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / methanol / 3 h / 0 °C

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

3: 90 percent / NaBH₄ / ethanol / 3 h / Ambient temperature

4: 73 percent / NaH / 1 h / Ambient temperature

5: 90 percent / O₃ / various solvent(s) / 1 h / -78 °C

6: 78 percent / 4 h / -78 °C

7: 76 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; sodium tetrahydroborate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; In methanol; ethanol;
DOI:10.1016/S0960-894X(97)10077-4

Reference yield:

: 198469-37-3
(3aR,5S,7R,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol

: 198469-41-9
(4aR,5R,7S,8aR)-5-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-7-[2-methyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxymethyl]-hexahydro-benzo[1,4]dioxin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 73 percent / NaH / 1 h / Ambient temperature

2: 90 percent / O₃ / various solvent(s) / 1 h / -78 °C

3: 78 percent / 4 h / -78 °C

4: 76 percent / AgOTf / 0 °C

5: 86 percent / aq. AcOH / 2 h / 80 °C

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

With silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; ozone; acetic acid; In various solvent(s);
DOI:10.1016/S0960-894X(97)10077-4