2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester

Base Information

• Chemical Name: 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester
• CAS No.: 205693-52-3
• Molecular Formula: C₇₁H₉₄O₁₀Si
• Molecular Weight: 1135.61

Synonyms:2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester

Chemical Property of 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester

There total 19 articles about 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl 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:

2-Benzyloxy-6-{(R)-16-[(2R,3S,4S,5R)-3,4,6-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-hexanoyloxy]-heptadecyl}-benzoic acid benzyl ester (205693-51-2) → 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester (205693-52-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jo9800098

Reference yield:

13-tetradecenyl magnesium bromide → 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester (205693-52-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 86 percent / CuCl(COD) / tetrahydrofuran / -78 - 20 °C

2.1: 94 percent / imidazole / dimethylformamide / 20 °C

3.1: [9-H-9-BBN]2 / tetrahydrofuran

3.2: 86 percent / NaOMe; KBr / PdCl₂(dppf) / tetrahydrofuran / Heating

4.1: NaH / dimethylformamide / 0.5 h / 0 - 20 °C

4.2: 92 percent / dimethylformamide / 3 h / 20 °C

5.1: 93 percent / K₂CO₃ / dimethylformamide / 4 h / Heating

6.1: 89 percent / TBAF / tetrahydrofuran / 15 h / 20 °C

7.1: 1468 mg / DMAP / CH₂Cl₂ / 16 h / 0 - 20 °C

8.1: 1007 mg / DDQ / CH₂Cl₂; H₂O / 3.5 h / 0 - 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; CuCl(COD); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Addition / 2.1: silylation / 3.1: Addition / 3.2: Suzuki reaction / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Etherification / 6.1: desilylation / 7.1: Esterification / 8.1: Oxidation;

DOI:10.1021/jo9800098

Reference yield:

3,4,6-tri-O-benzyl-D-glucitol (61008-72-8) → 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester (205693-52-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / conc. H₂SO₄; molecular sieves (3 Angstroem) / CH₂Cl₂ / 3.5 h / 20 °C

2: 91 percent / imidazole / dimethylformamide / 15 h / 20 °C

3: 62 percent / BH₃*THF / tetrahydrofuran / 2 h / Heating

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -65 - 0 °C

5: 1095 mg / NaClO₂; sulfamic acid / tetrahydrofuran; H₂O / 0.17 h / 20 °C

6: 1-dimethylamino-1-chloro-2-methyl-1-propene / CH₂Cl₂ / 1.5 h / 20 °C

7: 1468 mg / DMAP / CH₂Cl₂ / 16 h / 0 - 20 °C

8: 1007 mg / DDQ / CH₂Cl₂; H₂O / 3.5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium chlorite; borane-THF; oxalyl dichloride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; 3 A molecular sieve; sulfuric acid; aminosulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Cyclization / 2: silylation / 3: Reduction / 4: Swern oxidation / 5: Oxidation / 6: Chlorination / 7: Esterification / 8: Oxidation;

DOI:10.1021/jo9800098

upstream raw materials:

2-Benzyloxy-6-{(R)-16-[(2R,3S,4S,5R)-3,4,6-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-hexanoyloxy]-heptadecyl}-benzoic acid benzyl ester

3,4,6-tri-O-benzyl-D-glucitol

3,4,6-tri-O-benzyl-D-glucopyranose

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

Downstream raw materials:

2-Benzyloxy-6-{(R)-16-[(2R,3S,4S,5R)-3,4,6-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-trifluoromethanesulfonyloxy-hexanoyloxy]-heptadecyl}-benzoic acid benzyl ester

2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester

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