(R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester

Base Information

• Chemical Name: (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester
• CAS No.: 143465-60-5
• Molecular Formula: C₇₀H₉₆NO₁₃P
• Molecular Weight: 1190.5
• Mol file: 143465-60-5.mol

Synonyms:(R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester

Chemical Property of (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester

There total 9 articles about (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl 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: 74.0%

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid (111247-11-1) + Phosphoric acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-8-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yl ester diphenyl ester (143465-59-2) → (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester (143465-60-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/0040-4039(92)80009-9

Reference yield:

(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-5-C-hydroxymethyl-1,3,4-cyclohexanetriol (143465-64-9) → (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester (143465-60-5)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂, HCl / 20percent Pd(OH)2 / methanol

2: 62 percent / DIEA / dimethylformamide

3: 50 percent / p-TsOH / dimethylformamide

4: 1.) n-BuLi / 1.) THF, -78 deg C

5: 74 percent / EtNCN(CH₂)NMe₂*HCl, DMAP / CH₂Cl₂

With hydrogenchloride; dmap; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(92)80009-9

Reference yield:

(3aS,4R,5R,7aS)-3-Benzyl-4,5-bis-benzyloxy-6-hydroxymethyl-hexahydro-benzooxazol-2-one (106265-22-9,106295-31-2,143465-48-9,143465-62-7) → (R)-3-Benzyloxymethoxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-6-(diphenoxy-phosphoryloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester (143465-60-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / NaOH / ethanol / Heating

2: H₂, HCl / 20percent Pd(OH)2 / methanol

3: 62 percent / DIEA / dimethylformamide

4: 50 percent / p-TsOH / dimethylformamide

5: 1.) n-BuLi / 1.) THF, -78 deg C

6: 74 percent / EtNCN(CH₂)NMe₂*HCl, DMAP / CH₂Cl₂

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(92)80009-9

upstream raw materials:

(3R)-3-(Benzyloxymethoxy)tetradecanoic acid

Phosphoric acid (2R,4aR,6S,7R,8R,8aR)-7-((R)-3-benzyloxymethoxy-tetradecanoylamino)-8-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yl ester diphenyl ester

benzaldehyde dimethyl acetal

(1S,2S,3R,4R,5R)-2-amino-5-C-hydroxymethyl-1,3,4-cyclohexanetriol hydrochloride

Downstream raw materials:

(R)-3-Hydroxy-tetradecanoic acid (1R,2R,3S,5R,6R)-3-(diphenoxy-phosphoryloxy)-6-hydroxy-5-hydroxymethyl-2-((R)-3-hydroxy-tetradecanoylamino)-cyclohexyl ester

1D-(1,2,4/3,5)-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamido>-1-O-phosphono-5-C-hydroxymethyl-1,3,4-cyclohexanetriol