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

Base Information

• Chemical Name: D-Glucitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 1,4-dimethanesulfonate
• CAS No.: 149625-45-6
• Molecular Formula: C₂₃H₃₇NO₁₁S₂
• Molecular Weight: 567.679
• Mol file: 149625-45-6.mol

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

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

Chemical Property:

• PSA: 169.52000
• LogP: 4.49010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 9 articles about D-Glucitol, 2-deoxy-2-(1,1-dimethylethoxy)carbonylamino-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-, 1,4-dimethanesulfonate 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:

di-tert-butyl dicarbonate (24424-99-5) → 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-glucitol (149625-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / dioxane; H₂O / Ambient temperature

2: 82 percent / pyridine

With potassium hydrogencarbonate; In 1,4-dioxane; pyridine; water;

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) → 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-glucitol (149625-45-6)

Guidance literature:

Multi-step reaction with 7 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: 82 percent / pyridine

With sodium hydroxide; sodium tetrahydroborate; sodium hydride; potassium hydrogencarbonate; acetic acid; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide;

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

Reference yield:

(1S,2R,3S)-3-Amino-2-benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butane-1,4-diol → 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-glucitol (149625-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / dioxane; H₂O / Ambient temperature

2: 82 percent / pyridine

With potassium hydrogencarbonate; In 1,4-dioxane; pyridine; water;

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

upstream raw materials:

di-tert-butyl dicarbonate

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:

2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-galactitol

3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-1,2,4-trideoxy-5,6-O-isopropylidene-D-glucitol