(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

Base Information

Chemical Name:(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester
CAS No.:179530-65-5
Molecular Formula:C₇₇H₁₁₃NO₁₃
Molecular Weight:1260.74
Hs Code.:

(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

Synonyms:(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

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Chemical Property of (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

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Technology Process of (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

There total 13 articles about (2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl 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: 97.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 179530-62-2
(2S,3R,4R,5S,6R)-3-((R)-3-Benzyloxy-tetradecanoylamino)-5-hydroxy-6-hydroxymethyl-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

: 179530-65-5
(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

Guidance literature:: With pyridine; In dichloromethane; at 5 - 7 ℃; for 0.5h;
DOI:10.1016/S0040-4020(97)10063-1

Reference yield:

: 94715-57-8
O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate

: 179530-65-5
(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 9 steps

1: TMSOTf / CH₂Cl₂ / Ambient temperature

2: KOH / ethanol / 0.5 h / 24 °C

3: p-TsOH*H₂O / dimethylformamide / 16 h / 25 °C

4: 1.) Ph₃P, 2.) H₂O, 3.) DCC, DMAP, 4.) Et₃N

5: 1.) HCl / 1.) dioxane, H₂O, 60-65 deg C, 5 h, 2.) DMF, 55-60 deg C, 1 h

6: 44 percent / p-TsOH*H₂O / dimethylformamide / 16 h / 25 °C

7: 86 percent / DCC, DMAP / CH₂Cl₂ / 16 h / 25 °C

8: aq. AcOH / 1 h / 70 - 75 °C

9: 97 percent / pyridine / CH₂Cl₂ / 0.5 h / 5 - 7 °C

With pyridine; hydrogenchloride; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)10063-1

Reference yield:

: 94715-56-7
3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

: 179530-65-5
(2S,3R,4R,5S,6R)-6-Benzyloxycarbonyloxymethyl-3-((R)-3-benzyloxy-tetradecanoylamino)-5-hydroxy-4-((R)-3-tetradecanoyloxy-tetradecanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 9 steps

1: TMSOTf / CH₂Cl₂ / Ambient temperature

2: KOH / ethanol / 0.5 h / 24 °C

3: p-TsOH*H₂O / dimethylformamide / 16 h / 25 °C

4: 1.) Ph₃P, 2.) H₂O, 3.) DCC, DMAP, 4.) Et₃N

5: 1.) HCl / 1.) dioxane, H₂O, 60-65 deg C, 5 h, 2.) DMF, 55-60 deg C, 1 h

6: 44 percent / p-TsOH*H₂O / dimethylformamide / 16 h / 25 °C

7: 86 percent / DCC, DMAP / CH₂Cl₂ / 16 h / 25 °C

8: aq. AcOH / 1 h / 70 - 75 °C

9: 97 percent / pyridine / CH₂Cl₂ / 0.5 h / 5 - 7 °C

With pyridine; hydrogenchloride; dmap; potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)10063-1