3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol

Base Information

• Chemical Name: 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol
• CAS No.: 78038-33-2
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 78038-33-2.mol

Synonyms:3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol

Chemical Property of 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol

There total 12 articles about 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol 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: 87.0%

methyl 5-O-benzyl-3-deoxy-L-erythro-pentofuranoside (163956-65-8) → 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol (78038-33-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; for 44h; Ambient temperature;

Reference yield:

5-O-benzyl-3-deoxy-1,2-O-isopropylidene-4-O-(methylsulfonyl)-D-pentitol (77977-37-8,81275-21-0,81275-30-1) → 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol (78038-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90percent trifluoroacetic acid / Ambient temperature

2: CH₃ONa / methanol / 24 h / Ambient temperature

With sodium methylate; trifluoroacetic acid; In methanol;

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

Reference yield:

5-O-benzyl-3-deoxy-4-O-mesyl-D-pentitol (77977-38-9) → 3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol (78038-33-2) + (2R,4R)-2-benzyloxymethyl-4-hydroxytetrahydrofuran (78038-34-3)

Guidance literature:

With sodium methylate; In methanol; for 24h; Ambient temperature;

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

upstream raw materials:

5-O-benzyl-3-deoxy-4-O-mesyl-D-pentitol

5-O-benzyl-3-deoxy-1,2-O-isopropylidene-4-O-(methylsulfonyl)-D-pentitol

methyl 5-O-benzyl-3-deoxy-L-erythro-pentofuranoside

3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-lyxo-hexose

Downstream raw materials:

(2S,4S)-4-amino-2-(benzyloxymethyl)tetrahydrofuran-4-carboxilic acid

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

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

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

Refernces

• 1、 Yoshimura, Juji,Kondo, Shiro,Ihara, Masaki,Hashimoto, Hironobu. "SYNTHESIS OF FOUR STEREOISOMERS OF 4-AMINO-2-(HYDROXY-METHYL)TETRAHYDROFURAN-4-CARBOXYLIC ACID". . p. 129 - 142. Retrieved 2007/10/02.