4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester
• CAS No.: 313677-59-7
• Molecular Formula: C₃₁H₃₅NO₈
• Molecular Weight: 549.621
• Mol file: 313677-59-7.mol

Synonyms:4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester

Chemical Property of 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester

There total 8 articles about 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl 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: 95.0%

(S)-1-Benzyloxy-6-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-hexan-2-ol (313677-47-3) + 4-nitro-benzoic acid (62-23-7) → 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester (313677-59-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)01344-7

Reference yield:

(S)-5-Benzyloxy-4-tert-butyldimethylsiloxy-1-pentyne (124662-63-1) → 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester (313677-59-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

2: 78 percent / H₂ / Pd-C / ethyl acetate

3: TEA; DMAP / CH₂Cl₂

4: TBAF / tetrahydrofuran

5: 95 percent / DEAD; PPh₃ / tetrahydrofuran

With dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Alkylation / 2: Catalytic hydrogenation / 3: mesylation / 4: Substitution / 5: Esterification;

DOI:10.1016/S0040-4039(00)01344-7

Reference yield:

(S)-5-Benzyloxy-4-hydroxy-1-pentyne (124662-61-9) → 4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester (313677-59-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / NaH / tetrahydrofuran

2: 60 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

3: 78 percent / H₂ / Pd-C / ethyl acetate

4: TEA; DMAP / CH₂Cl₂

5: TBAF / tetrahydrofuran

6: 95 percent / DEAD; PPh₃ / tetrahydrofuran

With dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Etherification / 2: Alkylation / 3: Catalytic hydrogenation / 4: mesylation / 5: Substitution / 6: Esterification;

DOI:10.1016/S0040-4039(00)01344-7

upstream raw materials:

(S)-1-Benzyloxy-6-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-hexan-2-ol

4-nitro-benzoic acid

(S)-5-Benzyloxy-4-tert-butyldimethylsiloxy-1-pentyne

(S)-5-Benzyloxy-4-hydroxy-1-pentyne

Downstream raw materials:

(R)-1-Benzyloxy-6-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-hexan-2-ol