Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester

Base Information

• Chemical Name: Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester
• CAS No.: 856426-92-1
• Molecular Formula: C₃₆H₆₀O₈Si
• Molecular Weight: 648.953

Synonyms:Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester

Chemical Property of Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester

Chemical Property:

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Technology Process of Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester

There total 18 articles about Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl 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:

1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propan-2-ol → Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester (856426-92-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 2.89 g / tetra-n-propylammonium perruthenate; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

3.1: 87 percent / 4-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

4.1: 99 percent / SmI₂ / tetrahydrofuran; methanol / 0.25 h / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 13 h / 0 - 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

7.1: NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.5 h / 0 °C

7.2: 0.61 g / tetrahydrofuran; CH₂Cl₂ / 9 h / 20 °C

8.1: 9-BBN-H / tetrahydrofuran / 4 h / 20 °C

8.2: 1.74 g / H₂O₂; aq. NaOH / tetrahydrofuran / 12 h / 20 °C

9.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 20 °C

10.1: 1.75 g / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

11.1: Et₃N / tetrahydrofuran / 1.5 h / 20 °C

12.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

13.1: DIBALH / CH₂Cl₂; hexane / 0.33 h / -78 °C

14.1: 0.42 g / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 7.2: Wittig reaction / 9.1: Parikh-Doering oxidation;

DOI:10.1016/j.tet.2007.02.039

Reference yield:

(E)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester (856426-85-2) → Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester (856426-92-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / TMSCl; bis(N-isopropylsalicylaldimine) copper(II) complex / tetrahydrofuran; diethyl ether / 1.5 h / -45 °C

2.1: 95 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: KOt-Bu / tetrahydrofuran / 0.17 h / 20 °C

3.2: 90 percent / Bu₄NI / tetrahydrofuran / 1 h / 20 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 0.33 h / -78 °C

7.1: 0.42 g / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

With pyridine; dmap; chloro-trimethyl-silane; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/j.tet.2007.02.039

Reference yield:

((2R,3S,4aR,8aS)-2-Allyl-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane (856426-90-9) → Acetic acid 1-[(2S,3R)-2-((S)-3-benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-[(2R,3S,4aR,8aS)-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-propyl ester (856426-92-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 9-BBN-H / tetrahydrofuran / 4 h / 20 °C

1.2: 1.74 g / H₂O₂; aq. NaOH / tetrahydrofuran / 12 h / 20 °C

2.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 20 °C

3.1: 1.75 g / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

4.1: Et₃N / tetrahydrofuran / 1.5 h / 20 °C

5.1: 0.85 g / DMAP / tetrahydrofuran / 2 h / 20 °C

6.1: DIBALH / CH₂Cl₂; hexane / 0.33 h / -78 °C

7.1: 0.42 g / DMAP; pyridine / CH₂Cl₂; hexane / -78 - 0 °C

With pyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; pyridine-SO₃ complex; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 2.1: Parikh-Doering oxidation;

DOI:10.1016/j.tet.2007.02.039

upstream raw materials:

1-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-propan-2-one

(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-ol

(E)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

((2R,3S,4aR,8aS)-2-Allyl-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane

(2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

(E)-3-((2R,3S,4aR,8aS)-2-{3-[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-3-methyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid methyl ester

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