1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose

Base Information

• Chemical Name: 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose
• CAS No.: 121654-02-2
• Molecular Formula: C₁₉H₂₈O₅Si
• Molecular Weight: 364.514
• Mol file: 121654-02-2.mol

Synonyms:1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose

Chemical Property of 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose

There total 1 articles about 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose 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: 98.0%

tert-Butyl-dimethyl-((2R,4aR,8S,8aR)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-silane (121702-70-3) → 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose (121654-02-2)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 ℃; for 1h;

DOI:10.1021/ja00199a028

Reference yield:

1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose (121654-02-2) → Methyl 2-O-acetyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-α-D-altropyranoside (121654-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2 h / Ambient temperature

2: pyridine / 3 h / 0 °C

With pyridine;

DOI:10.1021/ja00199a028

Reference yield:

methanol (67-56-1) + 1,2-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-β-D-altropyranose (121654-02-2) → (2R,4aR,6S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (89872-83-3,101695-96-9,108739-93-1,112711-35-0)

Guidance literature:

for 2h; Yield given; Ambient temperature;

DOI:10.1021/ja00199a028

upstream raw materials:

tert-Butyl-dimethyl-((2R,4aR,8S,8aR)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-silane

Downstream raw materials:

(2R,4aR,6S,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Methyl 2-O-acetyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-α-D-altropyranoside