(R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde

Base Information

• Chemical Name: (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde
• CAS No.: 153941-93-6
• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.476
• Mol file: 153941-93-6.mol

Synonyms:

Chemical Property of (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde

There total 5 articles about (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde 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 bromide (100-39-0) → (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde (153941-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NaH / dimethylformamide / 1 h / Ambient temperature

2: 1.) MeOTf, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) CH₃CN, r.t., 10 min, 2.) MeOH, 0 deg C, 10 min, 3.) CH₃CN/H₂O, r.t., 10 min

With sodium tetrahydroborate; sodium hydride; methyl trifluoromethanesulfonate; copper(II) oxide; copper dichloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79321-X

Reference yield:

(R)-2-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-thiazol-2-yl-ethanol → (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde (153941-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NaH / dimethylformamide / 1 h / Ambient temperature

2: 1.) MeOTf, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) CH₃CN, r.t., 10 min, 2.) MeOH, 0 deg C, 10 min, 3.) CH₃CN/H₂O, r.t., 10 min

With sodium tetrahydroborate; sodium hydride; methyl trifluoromethanesulfonate; copper(II) oxide; copper dichloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79321-X

Reference yield:

2-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-thiazol-2-yl-ethanone → (R)-2-Benzyloxy-3-[(3aR,4S,6R,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-propionaldehyde (153941-93-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 33 percent Turnov_. / LiAl(tBuO)3H / tetrahydrofuran / 5 h / -75 - -35 °C / diastereoselectivity of reduction with various metal hydride

2: 92 percent / NaH / dimethylformamide / 1 h / Ambient temperature

3: 1.) MeOTf, 2.) NaBH₄, 3.) CuCl₂, CuO / 1.) CH₃CN, r.t., 10 min, 2.) MeOH, 0 deg C, 10 min, 3.) CH₃CN/H₂O, r.t., 10 min

With sodium tetrahydroborate; sodium hydride; lithium tri-t-butoxyaluminum hydride; methyl trifluoromethanesulfonate; copper(II) oxide; copper dichloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79321-X

upstream raw materials:

benzyl bromide

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose