[(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 286961-59-9
• Molecular Formula: C₂₉H₄₁NO₆Si
• Molecular Weight: 527.733
• Mol file: 286961-59-9.mol

Synonyms:[(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property of [(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 1 articles about [(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester 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: 91.0%

Methyltriphenylphosphonium bromide (1779-49-3) + [(2S,3R,4R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (286961-77-1) → [(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (286961-59-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.1246/cl.2000.646

Reference yield: 93.0%

[(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (286961-59-9) → ((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-2-methoxy-5-methylene-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (286961-78-2)

Guidance literature:

With hydrogenchloride; In methanol; for 0.166667h;

DOI:10.1246/cl.2000.646

Reference yield:

[(2S,3R,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-methylene-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (286961-59-9) → ((1S,2S,3S,6S)-2-Benzyloxy-3-benzyloxymethyl-6-hydroxy-4-oxo-cyclohexyl)-carbamic acid benzyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / 1 percent HCl / methanol / 0.17 h

2.1: 90 percent / PBu₃ / tetrahydrofuran / 1 h

3.1: BH₃*THF / tetrahydrofuran / 1 h / 0 - 45 °C

3.2: 69 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 16 h / 45 °C

4.1: 84 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide / 18 h

5.1: 67 percent / HgCl₂ / tetrahydrofuran; H₂O / 13 h

6.1: 100 percent / DBU / toluene / 0.83 h / -30 °C

With hydrogenchloride; barium dihydroxide; borane-THF; tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; barium(II) oxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; 1.1: Hydrolysis / 2.1: Substitution / 3.1: hydroboration / 3.2: Oxidation / 4.1: Etherification / 5.1: Ferrier reaction / 6.1: Isomerization;

DOI:10.1246/cl.2000.646

upstream raw materials:

Methyltriphenylphosphonium bromide

[(2S,3R,4R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Downstream raw materials:

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-2-methoxy-5-methylene-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

((2S,3R,4S,5R)-4-Benzyloxy-5-hydroxymethyl-2-methoxy-6-methylene-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

((1S,2S,3R,6S)-2-Benzyloxy-3-benzyloxymethyl-6-hydroxy-4-oxo-cyclohexyl)-carbamic acid benzyl ester

((2S,3R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-2-methoxy-6-methylene-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester