Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

Base Information

• Chemical Name: Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester
• CAS No.: 900159-64-0
• Molecular Formula: C₄₃H₇₄O₅S₂Si
• Molecular Weight: 763.275

Synonyms:Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

Chemical Property of Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

Chemical Property:

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Technology Process of Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester

There total 39 articles about Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl 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: 92.0%

(R)-2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanol (900159-62-8) + acetic anhydride (108-24-7) → Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester (900159-64-0)

Guidance literature:

With dmap; acetic anhydride; In pyridine; at 20 ℃; for 24h;

DOI:10.1021/jo0605086

Reference yield:

2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanol → Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester (900159-64-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

2: 68 percent / borane-dimethyl sulfide / (S)-CBS-catalyst / tetrahydrofuran / 12 h / 15 °C

3: 92 percent / 4-(dimethylamino)pyridine; Ac₂O / pyridine / 24 h / 20 °C

With dmap; dimethylsulfide borane complex; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; (S)-CBS-catalyst; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo0605086

Reference yield:

2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanone (900159-63-9) → Acetic acid (R)-2-[(2R,4S,5S)-5-((S)-6-benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethyl ester (900159-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / borane-dimethyl sulfide / (S)-CBS-catalyst / tetrahydrofuran / 12 h / 15 °C

2: 92 percent / 4-(dimethylamino)pyridine; Ac₂O / pyridine / 24 h / 20 °C

With dmap; dimethylsulfide borane complex; acetic anhydride; (S)-CBS-catalyst; In tetrahydrofuran; pyridine;

DOI:10.1021/jo0605086

upstream raw materials:

(R)-2-[(2R,4S,5S)-5-((S)-6-Benzyloxy-5-methyl-hexyl)-4-methyl-tetrahydro-furan-2-yl]-1-{2-[(1R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-methylene-octyl]-[1,3]dithian-2-yl}-ethanol

acetic anhydride

(2R)-4-((2R)-2-[1-(tert-butyl)-1,1-dimethylsilyl]oxypentyl)-2-methyl-4-pentenal

(2R)-4-((2R)-2-[1-(tert-butyl)-1,1-dimethylsilyl]oxypentyl)-2-methyl-4-penten-1-ol

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