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

Base Information

Chemical Name:(3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol
CAS No.:725724-13-0
Molecular Formula:C₆₆H₉₀O₁₁
Molecular Weight:1059.43
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol

There total 18 articles about (3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol 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: 82.0%

: 725724-12-9
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

: 725724-13-0
(3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1021/jo0496392

Reference yield:

: 116761-24-1
(R)-3-(benzyloxy)butanoic acid methyl ester

: 725724-13-0
(3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol

Guidance literature:: Multi-step reaction with 9 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

9.1: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °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; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/jo0496392

Reference yield:

: 116757-62-1
(R)-3-O-benzyl-1,3-butanediol

: 725724-13-0
(3R,15S,21R)-15-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyloxy)-21-benzyloxy-3-(4-methoxybenzyloxy)docosan-1-ol

Guidance literature:: Multi-step reaction with 8 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

8.1: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

With pyridine; Wilkinson's catalyst; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; (R,R)-1,2-cyclohexanediamine based salen cobalt; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/jo0496392