a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate

Base Information

• Chemical Name: a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate
• CAS No.: 114869-95-3
• Molecular Formula: C24H29 N O8
• Molecular Weight: 459.496
• Mol file: 114869-95-3.mol

Synonyms:a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate

Chemical Property of a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate

Chemical Property:

• PSA: 112.55000
• LogP: 2.55300

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside 99% min ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-acetate

There total 11 articles about a-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-, 6-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: 59.0%

N-Acetylimidazole (2466-76-4) + methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (114869-95-3)

Guidance literature:

In dichloromethane; Heating;

DOI:10.1016/0008-6215(87)80268-9

Reference yield:

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) + acetyl chloride (75-36-5) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (114869-95-3)

Guidance literature:

With pyridine; In dichloromethane; at -55 - -50 ℃; Inert atmosphere;

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (114869-95-3)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

4: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

5: aq. AcOH

6: pyridine / CH₂Cl₂

With pyridine; hydrogenchloride; barium dihydroxide; camphor-10-sulfonic acid; sodium carbonate; acetic acid; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Hydrolysis / 6: Acetylation;

DOI:10.1016/S0960-894X(99)00550-8

upstream raw materials:

N-Acetylimidazole

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

acetic anhydride

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-((2S,3R,4S,5R,6S)-3,5-diacetoxy-6-acetoxymethyl-4-benzyloxy-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((4aS,6S,7R,8R,8aR)-8-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Refernces

• 1、 Koshida, Shuhei,Suda, Yasuo,Sobel, Michael,Ormsby, Julie,Kusumoto, Shoichi. "Synthesis of heparin partial structures and their binding activities to platelets". . p. 3127 - 3132. Retrieved 2007/10/03.