(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 898552-25-5
• Molecular Formula: C₂₈H₄₀O₅Si
• Molecular Weight: 484.708
• Mol file: 898552-25-5.mol

Synonyms:(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

There total 6 articles about (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-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: 100.0%

[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-methanol (898552-11-9) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde (898552-25-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol (898552-08-4) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde (898552-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: CSA / methanol / 2 h

3: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 3: Swern oxidation;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (898552-07-3) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde (898552-25-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / p-TsOH*H₂O / tetrahydrofuran; methanol; H₂O / 18 h

2: 2,6-lutidine / CH₂Cl₂ / 1.5 h

3: CSA / methanol / 2 h

4: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 4: Swern oxidation;

DOI:10.1016/j.tetlet.2006.04.018

upstream raw materials:

[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-methanol

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

benzyl bromide

Downstream raw materials:

(E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-ol

(E)-(S)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-ol

(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

(2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol