(3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• CAS No.: 153974-94-8
• Molecular Formula: C₂₃H₃₂O₉
• Molecular Weight: 452.502
• Mol file: 153974-94-8.mol

Synonyms:(3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Chemical Property of (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

There total 3 articles about (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-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: 36.0%

3,5-anhydro-1,2-O-isopropylidene-α-D-xylofuranose (4118-63-2) + benzyl alcohol (100-51-6,185532-71-2) → 5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (23202-83-7,2592-42-9) + (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (153974-94-8) + C31H44O13

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; toluene; at 80 ℃; for 19h; Yields of byproduct given;

DOI:10.1246/cl.1994.141

Reference yield:

5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose (50600-39-0) → (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (153974-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOH / ethanol; H₂O / Ambient temperature

2: 36 percent / KOH / toluene; dimethylsulfoxide / 19 h / 80 °C

With potassium hydroxide; sodium hydroxide; In ethanol; water; dimethyl sulfoxide; toluene;

DOI:10.1246/cl.1994.141

Reference yield:

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose (6893-65-8,20513-95-5,20513-96-6,34981-06-1,40429-51-4,110349-61-6) → (3aR,5R,6S,6aR)-5-((3aR,5R,6S,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (153974-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOH / ethanol; H₂O / Ambient temperature

2: 36 percent / KOH / toluene; dimethylsulfoxide / 19 h / 80 °C

With potassium hydroxide; sodium hydroxide; In ethanol; water; dimethyl sulfoxide; toluene;

DOI:10.1246/cl.1994.141

upstream raw materials:

3,5-anhydro-1,2-O-isopropylidene-α-D-xylofuranose

benzyl alcohol

5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose

Downstream raw materials:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose