(2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

Base Information

• Chemical Name: (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde
• CAS No.: 94283-95-1
• Molecular Formula: C₂₇H₂₈O₅
• Molecular Weight: 432.516

Synonyms:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

Chemical Property of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

Chemical Property:

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Technology Process of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

There total 13 articles about (2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 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: 100.0%

methyl 3,4,6-tri-O-benzyl-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside → (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde (37699-02-8,94273-27-5,94283-95-1,122194-15-4)

Guidance literature:

In pyridine; water; N,N-dimethyl-formamide; at 160 ℃; for 0.0833333h;

DOI:10.1016/S0008-6215(97)00054-2

Reference yield: 90.0%

Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester → (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde (37699-02-8,94273-27-5,94283-95-1,122194-15-4)

Guidance literature:

With pyridine; water; In N,N-dimethyl-formamide; at 160 ℃;

DOI:10.1021/jo00056a028

Reference yield: 79.0%

3'-Phenyl-2',3'-methanopropyl 2-O-<<(trifluoromethyl)sulfonyl>oxy>-3,4,6-tri-O-benzyl-β-D-glucopyranoside (136764-17-5,145920-53-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane (110659-58-0) + (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde (37699-02-8,94273-27-5,94283-95-1,122194-15-4)

Guidance literature:

With pyridine;

DOI:10.1021/ja00021a052

upstream raw materials:

3'-Phenyl-2',3'-methanopropyl 2-O-<<(trifluoromethyl)sulfonyl>oxy>-3,4,6-tri-O-benzyl-β-D-glucopyranoside

N,N-dimethyl-formamide

tert-butylchlorodiphenylsilane

benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside

Downstream raw materials:

((3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol

2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol

2,5-anhydro-4,5-di-O-benzoyl-D-glucitol

2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol

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