(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 86030-96-8
• Molecular Formula: C₂₃H₃₀O₄Si
• Molecular Weight: 398.574
• Mol file: 86030-96-8.mol

Synonyms:(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

There total 4 articles about (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-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: 95.0%

methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside (86030-94-6) → (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde (86030-96-8)

Guidance literature:

With dipyridine chromium trioxide; In dichloromethane; for 1h;

DOI:10.1016/S0040-4039(00)85585-9

Reference yield:

methyl 2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexopyranoside (86030-92-4) → (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde (86030-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 1.)NaH, 2.)t-butyldiphenylsilyl chloride / tetrahydrofuran / 12 h / Ambient temperature

2: MeOH / p-toluenesulfonic acid / 12 h

3: 95 percent / CrO₃-2Pyr / CH₂Cl₂ / 1 h

With methanol; dipyridine chromium trioxide; sodium hydride; tert-butylchlorodiphenylsilane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)85585-9

Reference yield:

tert-Butyl-((2S,4R,6S)-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-diphenyl-silane (86030-93-5) → (2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde (86030-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: MeOH / p-toluenesulfonic acid / 12 h

2: 95 percent / CrO₃-2Pyr / CH₂Cl₂ / 1 h

With methanol; dipyridine chromium trioxide; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)85585-9

upstream raw materials:

methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside

methyl 2,4-dideoxy-6-O-(triphenylmethyl)-α-D-erythro-hexopyranoside

tert-Butyl-((2S,4R,6S)-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-diphenyl-silane

methyl 3,4-anhydro-2-deoxy-6-O-(triphenylmethyl)-α-D-ribo-hexopyranoside

Downstream raw materials:

(4R,6R)-6-(2-cyclohexylethyl)-4-hydroxytetrahydropyran-2-one

tert-Butyl-((2R,4R,6R)-2-methoxy-6-phenethyl-tetrahydro-pyran-4-yloxy)-diphenyl-silane

tert-Butyl-[(2R,4R,6R)-2-(2-cyclohexyl-ethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-diphenyl-silane

tert-Butyl-((2R,4R,6R)-2-methoxy-6-pentyl-tetrahydro-pyran-4-yloxy)-diphenyl-silane

Refernces