Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 191216-67-8
• Molecular Formula: C₆₅H₆₃NO₁₄S
• Molecular Weight: 1114.28
• Mol file: 191216-67-8.mol

Synonyms:Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-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: 65.0%

Succinic acid (4aR,6S,7R,8R,8aS)-6-benzyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester → Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (191216-67-8)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00729-6

Reference yield:

Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (127299-77-8,130781-28-1,138181-68-7,130781-27-0) → Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (191216-67-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / DMAP / pyridine / 48 h / Heating

2: 69 percent / DMAP, TosOH, DCC / pyridine / 24 h / 10 - 20 °C

3: 65 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature

With hydrogenchloride; dmap; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; diethyl ether;

DOI:10.1016/S0040-4039(97)00729-6

Reference yield:

Succinic acid mono-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl) ester (191216-55-4) → Succinic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (191216-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / DMAP, TosOH, DCC / pyridine / 24 h / 10 - 20 °C

2: 65 percent / NaCNBH₃, HCl / diethyl ether; tetrahydrofuran / 0.17 h / Ambient temperature

With hydrogenchloride; dmap; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; diethyl ether;

DOI:10.1016/S0040-4039(97)00729-6

upstream raw materials:

Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Succinic acid mono-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl) ester