(2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran

Base Information

• Chemical Name: (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran
• CAS No.: 72369-97-2
• Molecular Formula: C₁₄H₁₆N₂O₄
• Molecular Weight: 276.292
• Mol file: 72369-97-2.mol

Synonyms:(2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran

Chemical Property of (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran

There total 2 articles about (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran 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: 45.0%

carbon dioxide (124-38-9,18923-20-1) + copper(I) cyanide (544-92-3) + (2S)-benzyloxymethyl-4-oxo-tetrahydrofuran (72369-96-1) → (2S,4S)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran (72402-17-6) + (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran (72369-97-2)

Guidance literature:

With ammonium carbonate; In methanol; at 50 ℃; for 24h; under 38000 Torr; Heating;

DOI:10.1016/S0008-6215(00)81903-5

Reference yield:

(S)-5-Benzyloxymethyl-tetrahydro-furan-3-ol (72369-95-0,72370-00-4,78038-33-2,78038-34-3) → (2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran (72369-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / trifluoroacetic anhydride, dimethyl sulfoxide, triethylamine / CH₂Cl₂

2: 45 percent / ammonium carbonate / methanol / 24 h / 50 °C / 38000 Torr / Heating

With ammonium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)81903-5

Reference yield: 48.0%

(2S,4R)-2-benzyloxymethyl-4-C-(spiro-5-hydantoin)tetrahydrofuran (72369-97-2) → (3R,5S)-3-Amino-5-benzyloxymethyl-tetrahydro-furan-3-carboxylic acid (72369-98-3,72370-01-5,81275-27-6,81275-28-7)

Guidance literature:

With ammonium carbonate; barium dihydroxide; In water; at 100 ℃; for 0.5h; Heating;

DOI:10.1016/S0008-6215(00)81903-5

upstream raw materials:

carbon dioxide

copper(I) cyanide

(2S)-benzyloxymethyl-4-oxo-tetrahydrofuran

(S)-5-Benzyloxymethyl-tetrahydro-furan-3-ol

Downstream raw materials:

(3R,5S)-3-Amino-5-benzyloxymethyl-tetrahydro-furan-3-carboxylic acid