Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 183239-92-1
• Molecular Formula: C₃₃H₃₇NO₉
• Molecular Weight: 591.658
• Mol file: 183239-92-1.mol

Synonyms:Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 1 articles about Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 15.0%

benzoyl chloride (98-88-4) + 5-(benzyloxycarbonylamino)pentyl 4,6-O-benzylidene-β-D-glucopyranoside → Benzoic acid (2R,4aR,6R,7R,8R,8aR)-6-(5-benzyloxycarbonylamino-pentyloxy)-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester + Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (183239-92-1) + 5-(Benzyloxycarbonylamino)pentyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at -4 ℃; for 0.333333h;

DOI:10.1002/jlac.199619961016

Reference yield: 88.0%

Succinic acid mono-[(2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl] ester (183239-89-6) + Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (183239-92-1) → Succinic acid (2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (183239-93-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 26h; Ambient temperature;

DOI:10.1002/jlac.199619961016

Reference yield:

Benzoic acid (2R,4aR,6R,7R,8S,8aS)-6-(5-benzyloxycarbonylamino-pentyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (183239-92-1) → Benzoic acid (1R,3R,5S,6S,7R,8R,15S,16R,17R,19R)-7-benzyloxy-17-(5-benzyloxycarbonylamino-pentyloxy)-19-benzyloxymethyl-6-hydroxy-5-methyl-10,13-dioxo-2,4,9,14,18-pentaoxa-tricyclo[13.4.0.03,8]nonadec-16-yl ester (183240-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / DCC, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

2: 47 percent / HCl, NaCNBH₃, molecular sieves 3 Angstroem / diethyl ether; tetrahydrofuran / 0.08 h / Ambient temperature

3: 35 percent / N-iodosuccinimide, molecular sieves 3 Angstroem / acetonitrile / 21 h / 0 °C

With hydrogenchloride; dmap; N-iodo-succinimide; 3 A molecular sieve; sodium cyanoborohydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1002/jlac.199619961016

upstream raw materials:

benzoyl chloride

Downstream raw materials:

Succinic acid (2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Succinic acid (2R,3R,4S,5R,6R)-3-benzoyloxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Succinic acid (2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-2-ethylsulfanyl-5-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Succinic acid (2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4R,5S,6S)-4-benzyloxy-5-(2-chloro-acetoxy)-2-ethylsulfanyl-6-methyl-tetrahydro-pyran-3-yl ester