tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane
• CAS No.: 934808-43-2
• Molecular Formula: C₂₁H₃₅IO₅Si
• Molecular Weight: 522.496
• Mol file: 934808-43-2.mol

Synonyms:tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane

There total 1 articles about tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane 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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol (748154-79-2) → tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane (934808-43-2)

Guidance literature:

With lutidine; In dichloromethane;

DOI:10.1016/j.tetlet.2005.06.044

Reference yield: 99.0%

tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane (934808-43-2) → tert-butyl-[6-methoxy-5-(4-methoxy-benzyloxy)-2-methylene-tetrahydro-pyran-3-yloxy]-dimethyl-silane (863997-69-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/j.tet.2006.05.022

Reference yield:

tert-Butyl-[(2S,3S,5S,6S)-2-iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-dimethyl-silane (934808-43-2) → 6-hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone (863997-72-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / t-BuOK / tetrahydrofuran / 15 h / 20 °C

2: 70 percent / Hg(OCOCF₃)2 / acetone; H₂O / 9 h / 0 °C

3: 100 percent / triethylamine; mesyl chloride / CH₂Cl₂ / 1 h / 0 - 20 °C

4: 100 percent / AcOH; TBAF / tetrahydrofuran / 46 h / 0 - 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; acetic acid; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; 2: Ferrier carbocyclization;

DOI:10.1016/j.tet.2006.05.022

upstream raw materials:

t-butyldimethylsiyl triflate

(2S,3S,5S,6S)-2-Iodomethyl-6-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

Downstream raw materials:

tert-butyl-[6-methoxy-5-(4-methoxy-benzyloxy)-2-methylene-tetrahydro-pyran-3-yloxy]-dimethyl-silane

6-hydroxy-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-cyclohexanone