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

Base Information

• Chemical Name: (3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde
• CAS No.: 161939-00-0
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 161939-00-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-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:

benzyl 6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranoside (153289-40-8) → (3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde (161939-00-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In 1,2-dichloro-ethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)73734-8

Reference yield: 100.0%

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

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 1h; Ambient temperature;

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) → [5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione (130607-26-0)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium chlorite, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / Ambient temperature

2: Et₃N / tetrahydrofuran / 0 °C

3: ammonia / Ambient temperature

4: 2.) ammonia / 1.) (CH₂)2Cl₂, 80 deg C; 2.) (CH₂)2Cl₂, r.t.

5: 99 percent / HCl / propan-2-ol / 90 °C

6: H₂ / 10 percent Pd/C / ethanol / 3040 Torr / Ambient temperature

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ammonia; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; isopropyl alcohol; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)73734-8

upstream raw materials:

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

Downstream raw materials:

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

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

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

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