4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester
• CAS No.: 326853-49-0
• Molecular Formula: C₂₇H₃₁NO₈
• Molecular Weight: 497.545

Synonyms:4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

Chemical Property of 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

There total 21 articles about 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl 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: 82.0%

Acetic acid (R)-2-benzyloxy-1-[(2R,7S)-7-((S)-1-hydroxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-ethyl ester + 4-nitro-benzoic acid (62-23-7) → 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester (326853-49-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)01880-3

Reference yield:

benzyl bromide (100-39-0) → 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester (326853-49-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 76 percent / NaH / dimethylformamide

2.1: 88 percent / TEA; DMAP / CH₂Cl₂

3.1: 67 percent / Amberlyst 15 / methanol

4.1: 87 percent / K₂CO₃ / methanol; CH₂Cl₂

5.1: 96 percent / AgNO₃; pyridine / acetonitrile

6.1: 76 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

7.1: 99 percent / DMAP; Pyridine / CH₂Cl₂

8.1: 85 percent / TBAF / tetrahydrofuran

9.1: 99 percent / H₂ / Lindlar catalyst / methanol

10.1: (Bu₃Sn)2O / toluene / Heating

10.2: 97 percent / Zn(OTf)2 / 90 °C

11.1: 99 percent / TEA; DMAP / CH₂Cl₂

12.1: 81 percent / ZnBr₂ / 1,2-dichloro-ethane

13.1: 82 percent / DEAD; Ph₃P / tetrahydrofuran

With pyridine; dmap; n-butyllithium; Amberlyst 15; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; silver nitrate; triphenylphosphine; bis(tri-n-butyltin)oxide; zinc dibromide; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Yamaguchi reaction / 13.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(00)01880-3

Reference yield:

(4R,5R)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester (78469-78-0) → 4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-1-acetoxy-2-benzyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester (326853-49-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 67 percent / Amberlyst 15 / methanol

2.1: 87 percent / K₂CO₃ / methanol; CH₂Cl₂

3.1: 96 percent / AgNO₃; pyridine / acetonitrile

4.1: 76 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

5.1: 99 percent / DMAP; Pyridine / CH₂Cl₂

6.1: 85 percent / TBAF / tetrahydrofuran

7.1: 99 percent / H₂ / Lindlar catalyst / methanol

8.1: (Bu₃Sn)2O / toluene / Heating

8.2: 97 percent / Zn(OTf)2 / 90 °C

9.1: 99 percent / TEA; DMAP / CH₂Cl₂

10.1: 81 percent / ZnBr₂ / 1,2-dichloro-ethane

11.1: 82 percent / DEAD; Ph₃P / tetrahydrofuran

With pyridine; dmap; n-butyllithium; Amberlyst 15; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; silver nitrate; triphenylphosphine; bis(tri-n-butyltin)oxide; zinc dibromide; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; 4.1: Yamaguchi reaction / 11.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(00)01880-3

upstream raw materials:

4-nitro-benzoic acid

(4R,5R)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester

benzyl bromide

1-O-benzyl-2,3-O-isopropylidene-D-threitol

Downstream raw materials:

4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-2-acetoxy-1-methanesulfonyloxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

4-Nitro-benzoic acid (R)-1-[(2S,7R)-7-((R)-2-acetoxy-1-hydroxy-ethyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-propyl ester

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