1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

Base Information

• Chemical Name: 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose
• CAS No.: 126461-69-6
• Molecular Formula: C₁₉H₃₀O₄Si
• Molecular Weight: 350.53
• Mol file: 126461-69-6.mol

Synonyms:1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property of 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

There total 3 articles about 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose 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: 93.0%

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) + benzyl bromide (100-39-0) → 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose (126461-69-6)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In toluene; at 80 ℃; for 18h;

DOI:10.1016/S0040-4039(01)80733-4

Reference yield:

C24H50O4SiSn + benzyl bromide (100-39-0) → 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose (126461-69-6)

Guidance literature:

With tetrabutylammomium bromide; In toluene; at 125 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1080/07328303.2012.698438

Reference yield:

6-O-tert-butyldimethylsilyl-D-glucal (58871-09-3) → 1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose (126461-69-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 0.5 h / 125 °C / Microwave irradiation

2: tetrabutylammomium bromide / toluene / 0.17 h / 125 °C / Microwave irradiation

With tetrabutylammomium bromide; In toluene;

DOI:10.1080/07328303.2012.698438

upstream raw materials:

6-O-tert-butyldimethylsilyl-D-glucal

benzyl bromide

Downstream raw materials:

C₂₁H₃₂O₅Si

(S)-5-Benzyloxy-1-[(2R,4R,6S)-4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-pentan-2-ol

(R)-5-Benzyloxy-1-[(2R,4R,6S)-4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-pentan-2-ol

5-Benzyloxy-1-[(2R,4R,6S)-4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-pentan-2-ol