(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

Base Information

Chemical Name:(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
CAS No.:1054756-48-7
Molecular Formula:C₆₆H₈₈O₁₂
Molecular Weight:1073.42
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 19 articles about (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 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:

: 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

: 1054756-48-7
(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

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 0.333333h;
DOI:10.1021/jo0496392

Reference yield:

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

: 1054756-48-7
(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

Guidance literature:: Multi-step reaction with 10 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

10.1: 99.5 mg / Jones reagent / acetone / 0.33 h / 0 °C

With pyridine; Wilkinson's catalyst; lithium aluminium tetrahydride; n-butyllithium; jones reagent; 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; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo0496392

Reference yield:

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

: 1054756-48-7
(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

Guidance literature:: Multi-step reaction with 9 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

9.1: 99.5 mg / Jones reagent / acetone / 0.33 h / 0 °C

With pyridine; Wilkinson's catalyst; n-butyllithium; jones reagent; 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; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo0496392