(R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

Base Information

• Chemical Name: (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol
• CAS No.: 583843-85-0
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412
• Mol file: 583843-85-0.mol

Synonyms:(R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

Chemical Property of (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

There total 4 articles about (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 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: 68.0%

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (583843-85-0)

Guidance literature:

With water; acetic acid; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo802077t

Reference yield:

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (175877-45-9) → (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (583843-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2: aq. acetic acid / methanol / 18 h

With sodium hydride; acetic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo049159a

Reference yield:

benzyl bromide (100-39-0) → (R)-1-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol (583843-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaH / dimethylformamide / 3 h / 20 °C

2: aq. acetic acid / methanol / 18 h

With sodium hydride; acetic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo049159a

upstream raw materials:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

benzyl bromide

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

(3aR,5S,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

(R)-1-((3aR,5R,6R,6aR)-6-allyl-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(trityloxy)ethanol

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-(2-hydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(trityloxy)ethanol