(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile
• CAS No.: 82267-01-4
• Molecular Formula: C₂₇H₂₇NO₄
• Molecular Weight: 429.516

Synonyms:(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

Chemical Property of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

There total 18 articles about (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile 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: 75.0%

trimethylsilyl cyanide (7677-24-9) + Acetic acid (2S,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl ester (91110-24-6) → 2,5-anhydro-3,4,6-tri-O-benzyl-D-allononitrile (52492-43-0,52492-44-1,82267-01-4,82267-02-5,139189-60-9)

Guidance literature:

sodium periodate; tin(II) trifluoromethanesulfonate; lithium perchlorate; tin(IV) chloride; In dichloromethane; at -23 ℃; for 4h;

DOI:10.1246/cl.1989.145

Reference yield: 56.0%

trimethylsilyl cyanide (7677-24-9) + (3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate (58381-23-0) → (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile (82267-01-4) + 2,3,5-tri-O-benzyl-α-D-ribofuranosyl cyanide (82267-02-5)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -48 ℃; for 0.25h;

DOI:10.1021/jo802556s

Reference yield: 45.0%

2,3,5-tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-ribofuranose (51450-29-4) + trimethylsilyl cyanide (7677-24-9) → (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile (82267-01-4) + 2,3,5-tri-O-benzyl-α-D-ribofuranosyl cyanide (82267-02-5)

Guidance literature:

With boron trifluoride diethyl etherate; In nitromethane; Ambient temperature;

upstream raw materials:

mercury(II) cyanide

2,3,5-tri-O-benzyl-1-O-(p-nitrobenzoyl)-α,β-D-ribofuranose

trimethylsilyl cyanide

Acetic acid (2S,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl ester

Downstream raw materials:

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid

2,3,5-tri-O-benzyl-α-D-ribofuranosylmethanoic acid

1-Amino-2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-D-glucitol

1-deoxy-1-<(methoxyphenoxyphosphonyl)amino>-3,4,6-tri-O-benzyl-2,5-anhydro-D-glucitol

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