N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide

Base Information

• Chemical Name: N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide
• CAS No.: 175981-99-4
• Molecular Formula: C₃₅H₃₇NO₅
• Molecular Weight: 551.682

Synonyms:N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide

Chemical Property of N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide

Chemical Property:

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Technology Process of N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide

There total 8 articles about N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-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: 75.0%

acetic anhydride (108-24-7) + (2S,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran (175982-00-0) → N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide (175981-99-4)

Guidance literature:

With hydrogen; nickel;

DOI:10.1039/CC9960000347

Reference yield:

phenyllithium (591-51-5) → N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide (175981-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85.4 percent / toluene / 1 h / -78 °C

2: 91 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / 0.25 h / -40 °C

3: 75 percent / H₂ / Raney Ni

With triethylsilane; boron trifluoride diethyl etherate; hydrogen; nickel; In toluene; acetonitrile;

DOI:10.1039/CC9960000347

Reference yield:

(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8) → N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide (175981-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85.4 percent / toluene / 1 h / -78 °C

2: 91 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / 0.25 h / -40 °C

3: 75 percent / H₂ / Raney Ni

With triethylsilane; boron trifluoride diethyl etherate; hydrogen; nickel; In toluene; acetonitrile;

DOI:10.1039/CC9960000347

upstream raw materials:

acetic anhydride

(2S,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran

phenyllithium

(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide

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