D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate

Base Information

• Chemical Name: D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate
• CAS No.: 163707-61-7
• Molecular Formula: C23H35 N O8
• Molecular Weight: 453.53
• Mol file: 163707-61-7.mol

Synonyms:D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate

Chemical Property of D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate

Chemical Property:

• PSA: 112.55000
• LogP: 2.93150

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate

There total 14 articles about D-Galactitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 4-acetate 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: 67.0%

4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1-O-triphenylmethyl-D-galactitol (163707-60-6) → 4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-galactitol (163707-61-7)

Guidance literature:

With dimethoxypropane; toluene-4-sulfonic acid; In acetone; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

benzyl bromide (100-39-0) → 4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-galactitol (163707-61-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80percent oily NaH / dimethylformamide / Ambient temperature

2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1M aq. NaOH / methanol / 7 h / Heating

6: KHCO₃ / dioxane; H₂O / Ambient temperature

7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

10: 1M aq. NaOH / dioxane / 15 h / Heating

11: KHCO₃ / dioxane; H₂O / Ambient temperature

12: 100 percent / pyridine / 4 h / Ambient temperature

13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2) → 4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-galactitol (163707-61-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80percent oily NaH / dimethylformamide / Ambient temperature

2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1M aq. NaOH / methanol / 7 h / Heating

6: KHCO₃ / dioxane; H₂O / Ambient temperature

7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

10: 1M aq. NaOH / dioxane / 15 h / Heating

11: KHCO₃ / dioxane; H₂O / Ambient temperature

12: 100 percent / pyridine / 4 h / Ambient temperature

13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

upstream raw materials:

4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1-O-triphenylmethyl-D-galactitol

benzyl bromide

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

2-methyl-(3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2.1-d>-2-oxazoline

Downstream raw materials:

3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-galactitol

1,2-diamino-1,3-di-N,O-benzyl-2,4-N,O-carbonyl-1,2-deoxy-5,6-O-isopropylidene-D-glucitol

2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-5,6-O-isopropylidene-1-O-methanesulfonyl-D-glucitol

5,6-di-O-acetyl-2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-1-O-methanesulfonyl-D-glucitol