2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside
CAS No.:176490-60-1
Molecular Formula:C₃₆H₄₈O₆Si
Molecular Weight:604.859
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside 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:

: 176589-70-1
Acetic acid (3R,4S,5S,6R)-2,3,5-triacetoxy-6-((R)-1-allyloxy-ethyl)-tetrahydro-pyran-4-yl ester

: 176490-60-1
2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) acetic acid, hydrazine, 2.) Vilsmeier bromide, s-collidine / 1.) DMF, 50 deg C, 2 h, 2.) CH₂Cl₂, 2 h

2: silver trifluoromethanesulfonate, s-collidine / CH₂Cl₂ / 1 h / -28 °C

3: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

With 2,4,6-trimethyl-pyridine; Vilsmeier bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; hydrazine; In dichloromethane;
DOI:10.1021/ja00084a003

Reference yield:

: (3R,4S,5R,6S)-6-((R)-1-Allyloxy-ethyl)-tetrahydro-pyran-2,3,4,5-tetraol

: 176490-60-1
2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 4-(N,N-dimethylamino)pyridine, pyridine / 16 h

2: 1.) acetic acid, hydrazine, 2.) Vilsmeier bromide, s-collidine / 1.) DMF, 50 deg C, 2 h, 2.) CH₂Cl₂, 2 h

3: silver trifluoromethanesulfonate, s-collidine / CH₂Cl₂ / 1 h / -28 °C

4: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

With pyridine; 2,4,6-trimethyl-pyridine; dmap; Vilsmeier bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; hydrazine; In dichloromethane;
DOI:10.1021/ja00084a003

Reference yield:

: 153718-10-6
6-O-allyl-7-deoxy-1,2;3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

: 176490-60-1
2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 90percent aq. trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

2: 4-(N,N-dimethylamino)pyridine, pyridine / 16 h

3: 1.) acetic acid, hydrazine, 2.) Vilsmeier bromide, s-collidine / 1.) DMF, 50 deg C, 2 h, 2.) CH₂Cl₂, 2 h

4: silver trifluoromethanesulfonate, s-collidine / CH₂Cl₂ / 1 h / -28 °C

5: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

With pyridine; 2,4,6-trimethyl-pyridine; dmap; Vilsmeier bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; trifluoroacetic acid; hydrazine; In dichloromethane;
DOI:10.1021/ja00084a003