(R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde

Base Information

• Chemical Name: (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde
• CAS No.: 639476-02-1
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412

Synonyms:(R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde

Chemical Property of (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde

There total 4 articles about (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde 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: 83.0%

2-O-benzyl-3,4:5,6-di-O-isopropylidene-D-glucitol (276238-73-4) → (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde (639476-02-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.5h;

DOI:10.1021/jo034679b

Reference yield:

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0) → (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde (639476-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Ag₂O / CH₂Cl₂

2: 87 percent / LiAlH₄ / tetrahydrofuran

3: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

With lithium aluminium tetrahydride; Dess-Martin periodane; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034679b

Reference yield:

Methyl 3,4:5,6-di-O-isopropylidene-2-O-(benzyl)-D-gluconate (212832-94-5) → (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde (639476-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / LiAlH₄ / tetrahydrofuran

2: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

With lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034679b

upstream raw materials:

2-O-benzyl-3,4:5,6-di-O-isopropylidene-D-glucitol

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

Methyl 3,4:5,6-di-O-isopropylidene-2-O-(benzyl)-D-gluconate

D-Glucono-1,5-lactone

Downstream raw materials:

(2RS,4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidenenonan-2-ol

(4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidene-2-oxononane

N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide

N-Benzyl-N-[(1R,2S,3R,5R,7R)-2-benzyloxy-5-benzyloxymethyl-7-((R)-1,2-dihydroxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl]-acetamide

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