2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 502687-24-3
• Molecular Formula: C₄₆H₆₀O₇Si₂
• Molecular Weight: 781.149

Synonyms:2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 7 articles about 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl 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: 87.0%

(methoxymethyl)triphenylphosphonium chloride (4009-98-7) + 2,2-Dimethyl-propionic acid (2R,3S,3aR,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (502687-24-3)

Guidance literature:

(methoxymethyl)triphenylphosphonium chloride; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.166667h;

2,2-Dimethyl-propionic acid (2R,3S,3aR,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester; In tetrahydrofuran; at 0 - 20 ℃;

With potassium hydroxide; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo051479m

Reference yield: 87.0%

(methoxymethylene)triphenylphosphorane (20763-19-3) + 2,2-Dimethyl-propionic acid (2R,3S,3aR,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (502687-24-3)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol027389a

Reference yield:

[(2R,3S,3aR,5S,6R,6aR)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-5-triethylsilanyloxy-hexahydro-furo[3,2-b]furan-2-yl]-methanol (502687-22-1) → 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-[(E)-(S)-1-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-allyl]-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (502687-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

2.1: 875 mg / HCl / CH₂Cl₂; methanol / 0.25 h / 0 °C

3.1: KOtBu / tetrahydrofuran / 0.17 h / 0 °C

3.2: tetrahydrofuran / 0 - 20 °C

3.3: 87 percent / aq. KOH / tetrahydrofuran / 0.5 h

With hydrogenchloride; dmap; potassium tert-butylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3.2: Wittig reaction;

DOI:10.1021/jo051479m

upstream raw materials:

(methoxymethylene)triphenylphosphorane

(methoxymethyl)triphenylphosphonium chloride

2,2-Dimethyl-propionic acid (2R,3S,3aR,5S,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-triethylsilanyloxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester

(3R,3aR,6R,6aR)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3S,3aR,5R,6R,7R,7aR)-5,6-diacetoxy-3,7-bis-(tert-butyl-diphenyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-2-ylmethyl ester

[(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

2,2-Dimethyl-propionic acid (2R,3S,3aR,5S,6R,7R,7aR)-5,6-diacetoxy-3,7-bis-(tert-butyl-diphenyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-2-ylmethyl ester

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