benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside

Base Information

• Chemical Name: benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside
• CAS No.: 153289-43-1
• Molecular Formula: C₂₄H₂₈N₂O₇
• Molecular Weight: 456.496
• Mol file: 153289-43-1.mol

Synonyms:benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside

Chemical Property of benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside

There total 5 articles about benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside 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:

benzyl 6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranoside (153289-40-8) → benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside (153289-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to RT, 45 min

2: 100 percent / NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

3: Et₃N / tetrahydrofuran / 0.5 h / 0 - 20 °C

4: NH₃ gas / tetrahydrofuran / 0.5 h

5: 2.) NH₃ gas / 1.) CH₂Cl₂, a) RT, 30 min, b) 90 deg C, 2 h, 2.) CH₂Cl₂, RT

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; ammonia; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1016/0040-4020(95)00975-2

Reference yield:

(3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde (161939-00-0) → benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside (153289-43-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

2: Et₃N / tetrahydrofuran / 0.5 h / 0 - 20 °C

3: NH₃ gas / tetrahydrofuran / 0.5 h

4: 2.) NH₃ gas / 1.) CH₂Cl₂, a) RT, 30 min, b) 90 deg C, 2 h, 2.) CH₂Cl₂, RT

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ammonia; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1016/0040-4020(95)00975-2

Reference yield:

benzyl 5-O-benzyl-1-carboxyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside (153289-41-9) → benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside (153289-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / 0.5 h / 0 - 20 °C

2: NH₃ gas / tetrahydrofuran / 0.5 h

3: 2.) NH₃ gas / 1.) CH₂Cl₂, a) RT, 30 min, b) 90 deg C, 2 h, 2.) CH₂Cl₂, RT

With ammonia; triethylamine; In tetrahydrofuran;

DOI:10.1016/0040-4020(95)00975-2

upstream raw materials:

benzyl 6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranoside

(3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

benzyl 5-O-benzyl-1-carboxyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside

Downstream raw materials:

[5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione

benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-β-D-ribofuranoside