Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 725724-12-9
• Molecular Formula: C₈₂H₁₀₈O₁₁Si
• Molecular Weight: 1297.84

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester

There total 17 articles about Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-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: 62.0%

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (125164-10-5) + (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docosan-8-ol (725723-96-6) → Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester (725724-12-9) + Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; acetonitrile; at -40 ℃; for 2.5h;

DOI:10.1021/jo0496392

Reference yield:

(R)-3-(benzyloxy)butanoic acid methyl ester (116761-24-1) → Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester (725724-12-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 94 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

2.1: 77 percent / pyrdine / 3 h / 0 °C

3.1: magnesium / tetrahydrofuran

3.2: tetrahydrofuran / 0.5 h / 0 °C

3.3: 12.8 g / CuI / tetrahydrofuran / 15 h / 0 - 50 °C

4.1: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 24 h / 0 - 20 °C

5.1: 44 percent / (R,R)-1,2-cyclohexanediamine based salen cobalt complex; acetic acid / toluene / 1 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 91 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.1: 99 percent / tris(triphenylphosphine)rhodium chloride; H₂ / benzene / 10 h / 20 °C

8.1: 62 percent / molecular sieves 4 Angstroem; trimethylsilyl trifluoromethanesulfonate / acetonitrile; CH₂Cl₂ / 2.5 h / -40 °C

With pyridine; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; (R,R)-1,2-cyclohexanediamine based salen cobalt; 4 A molecular sieve; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/jo0496392

Reference yield:

(R)-3-O-benzyl-1,3-butanediol (116757-62-1) → Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(1S,13R)-1-((R)-6-benzyloxy-heptyl)-15-(tert-butyl-diphenyl-silanyloxy)-13-(4-methoxy-benzyloxy)-pentadecyloxy]-tetrahydro-pyran-2-ylmethyl ester (725724-12-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / pyrdine / 3 h / 0 °C

2.1: magnesium / tetrahydrofuran

2.2: tetrahydrofuran / 0.5 h / 0 °C

2.3: 12.8 g / CuI / tetrahydrofuran / 15 h / 0 - 50 °C

3.1: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 44 percent / (R,R)-1,2-cyclohexanediamine based salen cobalt complex; acetic acid / toluene / 1 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: 91 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.1: 99 percent / tris(triphenylphosphine)rhodium chloride; H₂ / benzene / 10 h / 20 °C

7.1: 62 percent / molecular sieves 4 Angstroem; trimethylsilyl trifluoromethanesulfonate / acetonitrile; CH₂Cl₂ / 2.5 h / -40 °C

With pyridine; Wilkinson's catalyst; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; (R,R)-1,2-cyclohexanediamine based salen cobalt; 4 A molecular sieve; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/jo0496392

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docosan-8-ol

p-Anisaldehyde dimethyl acetal

(R)-3-(benzyloxy)butanoic acid methyl ester

Downstream raw materials:

(3R,15S,21R)-15-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-21-benzyloxy-3-(4-methoxy-benzyloxy)-docosanoic acid

(3R,15S,21R)-21-benzyloxy-15-(2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-3-(4-methoxybenzyloxy)docosanoic acid

(3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol

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