(((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane

Base Information

• Chemical Name: (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane
• CAS No.: 855282-02-9
• Molecular Formula: C₃₀H₄₄O₅Si
• Molecular Weight: 512.762
• Mol file: 855282-02-9.mol

Synonyms:(((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane

Chemical Property of (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane

There total 11 articles about (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane 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: 75.0%

C29H42O6Si + Methylenetriphenylphosphorane (19493-09-5) → (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane (855282-02-9)

Guidance literature:

DOI:10.1016/j.tetlet.2007.08.077

Reference yield:

Acetic acid (4S,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxy-5-methoxymethoxy-3,3-dimethyl-tetrahydro-pyran-2-yl ester + allyl-trimethyl-silane (762-72-1) → (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane (855282-02-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja050728l

Reference yield:

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde (937166-57-9) → (((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane (855282-02-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / ZnBr₂ / CH₂Cl₂ / -78 - 0 °C

2.1: 98 percent / NaH / tetrahydrofuran

3.1: 98 percent / n-BuSH; ZnBr₂ / CH₂Cl₂ / 0.13 h / 20 °C

4.1: 80 percent / DIPEA / CH₂Cl₂ / 11 h / 20 °C

5.1: 91 percent / P₂O₅ / CH₂Cl₂ / 3 h / 20 °C

6.1: 83 percent / K₂CO₃ / methanol / 3 h / 20 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂ / -78 - 20 °C

8.1: DMAP / pyridine / 30 h / 20 °C

9.1: 861 mg / BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

With dmap; n-butanethiol; boron trifluoride diethyl etherate; phosphorus pentoxide; sodium hydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; zinc dibromide; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1021/ja050728l

upstream raw materials:

allyl-trimethyl-silane

Methylenetriphenylphosphorane

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde

(2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol