1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate

Base Information

• Chemical Name: 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate
• CAS No.: 107453-27-0
• Molecular Formula: C₃₄H₄₈O₆Si
• Molecular Weight: 580.837
• Mol file: 107453-27-0.mol

Synonyms:1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate

Chemical Property of 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate

There total 17 articles about 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate 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: 35.9%

(4ξ,6ξ,8ξ)-6,9-anhydro-8-<(tert-butyldiphenylsiloxy)methyl>-2,5,8,10-tetradeoxy-1,3-O-isopropylidene-2-methyl-6-C-methyl-D-glycero-D-threo-decoulode pivaloate (107441-81-6) → 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate (107453-27-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 1h;

DOI:10.1021/jo00385a024

Reference yield:

3-deoxy-3-methyl-D-threitol 2,4-dipivaloate (107441-64-5) → 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate (107453-27-0)

Guidance literature:

Multi-step reaction with 16 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.43 h / -78 °C

2: pyridine / benzene / 0.33 h / 5 °C

3: 90.5 percent / N-methoxymorpholine N-oxide, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 10.5 h

4: oxalyl chloride, DMSO / CH₂Cl₂ / -78 - 30 °C

5: CH₂Cl₂ / 1.33 h / -30 - 0 °C

6: 71.4 percent / LiBF₄, p-toluenesulfonic acid / acetone; CH₂Cl₂ / 12 h

7: LiAlH₄ / tetrahydrofuran / 4 h / -78 - 25 °C

8: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h

9: 73.8 percent / BaO, Ba(OH)2 / dimethylformamide / 1.) RT, 0.5 h, 2.) 40 deg C, 34 h

10: 74.5 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 28 h

11: 10percent aq. HCl / tetrahydrofuran / 26 h / 50 °C

12: p-toluenesulfonic acid / acetone; tetrahydrofuran / 6 h

13: 90.4 percent / H₂, acetic acid / 10percent Pd/C / ethyl acetate / 7 h

14: 91.4 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 2.25 h

15: 96.7 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.33 h / -78 °C

16: 35.9 percent / 10percent aq. HCl / tetrahydrofuran / 1 h

With pyridine; hydrogenchloride; barium dihydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; N',N'-dimethylaminopyridine; N-methoxymorpholine N-oxide; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jo00385a024

Reference yield:

(2R,3R)-1,3-dihydroxy-2-methyl-4-pentene dipivaloate (107441-66-7) → 1,7:6,9-dianhydro-8-<(tert-butyldiphenylsilyloxy)methyl>-2,5,8,10-tetradeoxy-2-methyl-6-C-methyl-α-D-threo-D-ido-7-decoulo-7,3-pyranose pivaloate (107453-27-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 90.5 percent / N-methoxymorpholine N-oxide, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 10.5 h

2: oxalyl chloride, DMSO / CH₂Cl₂ / -78 - 30 °C

3: CH₂Cl₂ / 1.33 h / -30 - 0 °C

4: 71.4 percent / LiBF₄, p-toluenesulfonic acid / acetone; CH₂Cl₂ / 12 h

5: LiAlH₄ / tetrahydrofuran / 4 h / -78 - 25 °C

6: 56.2 percent / p-toluenesulfonic acid / benzene / 22 h

7: 73.8 percent / BaO, Ba(OH)2 / dimethylformamide / 1.) RT, 0.5 h, 2.) 40 deg C, 34 h

8: 74.5 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 28 h

9: 10percent aq. HCl / tetrahydrofuran / 26 h / 50 °C

10: p-toluenesulfonic acid / acetone; tetrahydrofuran / 6 h

11: 90.4 percent / H₂, acetic acid / 10percent Pd/C / ethyl acetate / 7 h

12: 91.4 percent / N',N'-dimethylaminopyridine / CH₂Cl₂ / 2.25 h

13: 96.7 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.33 h / -78 °C

14: 35.9 percent / 10percent aq. HCl / tetrahydrofuran / 1 h

With hydrogenchloride; barium dihydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium tetrafluoroborate; oxalyl dichloride; N',N'-dimethylaminopyridine; N-methoxymorpholine N-oxide; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/jo00385a024

upstream raw materials:

(4ξ,6ξ,8ξ)-6,9-anhydro-8-<(tert-butyldiphenylsiloxy)methyl>-2,5,8,10-tetradeoxy-1,3-O-isopropylidene-2-methyl-6-C-methyl-D-glycero-D-threo-decoulode pivaloate

3-deoxy-3-methyl-D-threitol 2,4-dipivaloate

(2R,3R)-1,3-dihydroxy-2-methyl-4-pentene dipivaloate

3-deoxy-3-methyl-D-threose dipivaloate