N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide

Base Information

• Chemical Name: N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide
• CAS No.: 206751-94-2
• Molecular Formula: C₂₂H₂₇NO₆
• Molecular Weight: 401.459
• Mol file: 206751-94-2.mol

Synonyms:N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide

Chemical Property of N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide

There total 5 articles about N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide 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: 98.0%

N-((3aR,4R,6R,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide (206751-93-1) → N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide (206751-94-2)

Guidance literature:

With acetic acid; In water; at 50 ℃; for 0.666667h;

DOI:10.1016/S0008-6215(97)10017-9

Reference yield:

benzyl 2-acetamido-2-deoxy-β-D-galactopyranoside (41355-95-7,347411-88-5) → N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide (206751-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / (+/-)-camphor-10-sulfonic acid / 48 h / Ambient temperature

2: 85 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 20 h / Ambient temperature

3: 98 percent / acetic acid / H₂O / 0.67 h / 50 °C

With barium dihydroxide; camphor-10-sulfonic acid; acetic acid; barium(II) oxide; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10017-9

Reference yield:

benzyl bromide (100-39-0) → N-((2R,3R,4R,5R,6R)-2-Benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-3-yl)-acetamide (206751-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 20 h / Ambient temperature

2: 98 percent / acetic acid / H₂O / 0.67 h / 50 °C

With barium dihydroxide; acetic acid; barium(II) oxide; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10017-9

upstream raw materials:

N-((3aR,4R,6R,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide

benzyl 2-acetamido-2-deoxy-β-D-galactopyranoside

benzyl bromide

benzyl 2-acetamido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2R,3R,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl ester