(1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

Base Information

• Chemical Name: (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one
• CAS No.: 126267-14-9
• Molecular Formula: C₃₃H₃₇NO₇Si
• Molecular Weight: 587.745

Synonyms:(1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

Chemical Property of (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

There total 11 articles about (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one 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: 90.0%

tert-butyldiphenylsilyl triflate (92886-86-7) + 4-<(4S,5R,6R)-5-hydroxy-6-(benzoyloxymethyl)-1,3-dioxan-4-yl>-2,6-piperidinedione (126267-12-7) → (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-14-9)

Guidance literature:

With 2,3,5-trimethyl-pyridine; In dichloromethane; for 24h; Ambient temperature;

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-14-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 30percent HCl / tetrahydrofuran / 2 h / 20 °C

2: benzoic acid / toluene / 29 h / 22 °C

3: toluene, reflux, 30 min

4: H₂ / Pd/C / methanol

5: 94 percent / pyridine / 60 h / -10 °C

6: 90 percent / collidine / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; hydrogen; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;

Reference yield:

(E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate (102487-47-8) → (1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-(benzoyloxymethyl)-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (126267-14-9)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene, reflux, 30 min

2: H₂ / Pd/C / methanol

3: 94 percent / pyridine / 60 h / -10 °C

4: 90 percent / collidine / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; 2,3,5-trimethyl-pyridine; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

upstream raw materials:

tert-butyldiphenylsilyl triflate

4-<(4S,5R,6R)-5-hydroxy-6-(benzoyloxymethyl)-1,3-dioxan-4-yl>-2,6-piperidinedione

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

(1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2S)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,2S)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

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