(1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

Base Information

• Chemical Name: (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol
• CAS No.: 185155-21-9
• Molecular Formula: C₂₈H₃₄O₇
• Molecular Weight: 482.574
• Mol file: 185155-21-9.mol

Synonyms:(1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

Chemical Property of (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

There total 11 articles about (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol 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:

(1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol (185155-31-1) → (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol (185155-21-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h; Yield given;

DOI:10.1021/jo961534e

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose (138709-45-2) → (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol (185155-21-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.) NaHCO₃, aq. H₂O₂ / 1.) THF, -78 deg C, 30 min; -78 deg C to -15 deg C 2 h, 2.) THF, MeOH, reflux, 12 h

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

3: Ac₂O / 1.5 h / 68 °C

4: MeONa / methanol / 2 h / Ambient temperature

5: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

6: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

7: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

8: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

9: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

10: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

11: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; dipyridinium dichromate; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; acetic anhydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961534e

Reference yield:

1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose (168103-69-3) → (1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3,5-bis-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol (185155-21-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / imidazole / dimethylformamide / Ambient temperature

2: Ac₂O / 1.5 h / 68 °C

3: MeONa / methanol / 2 h / Ambient temperature

4: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

5: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

6: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

7: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

8: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

9: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

10: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; dipyridinium dichromate; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo961534e

upstream raw materials:

(1S,3R,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octan-4-ol

1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose

1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

1,6-Anhydro-2,3-di-O-benzyl-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-β-D-galactopyranose

Downstream raw materials:

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarbaldehyde

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-but-3-enyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid di-tert-butyl ester

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-4-hydroxy-1-(3-hydroxy-propyl)-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid di-tert-butyl ester