N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 556039-04-4
• Molecular Formula: C₃₄H₃₉NO₈S
• Molecular Weight: 621.752
• Mol file: 556039-04-4.mol

Synonyms:N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

There total 7 articles about N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl 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:

benzylamine (100-46-9) + Succinic acid mono-[(2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl] ester (556039-09-9) → N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (556039-04-4)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1081/CAR-120019014

Reference yield:

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside (39698-00-5) → N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (556039-04-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 82 percent / BF₃-Et₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 98 percent / sodium / methanol / 12 h / 20 °C

3.1: 94 percent / p-toluenesulfonic acid / acetonitrile / 0.5 h / 20 °C

4.1: LiAlH₄ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 4 h / Heating

4.2: 98 percent / AlCl₃ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 4 h / Heating

5.1: pyridine; N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 553 mg / HBTU; diisopropylethylamine / dimethylformamide / 2 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/CAR-120019014

Reference yield:

thiophenol (108-98-5) → N-Benzyl-succinamic acid (2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (556039-04-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 82 percent / BF₃-Et₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 98 percent / sodium / methanol / 12 h / 20 °C

3.1: 94 percent / p-toluenesulfonic acid / acetonitrile / 0.5 h / 20 °C

4.1: LiAlH₄ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 4 h / Heating

4.2: 98 percent / AlCl₃ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 4 h / Heating

5.1: pyridine; N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 553 mg / HBTU; diisopropylethylamine / dimethylformamide / 2 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/CAR-120019014

upstream raw materials:

benzylamine

Succinic acid mono-[(2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl] ester

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

thiophenol