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

Base Information

• Chemical Name: N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide
• CAS No.: 206751-89-5
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524
• Mol file: 206751-89-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-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: 91.0%

benzyl bromide (100-39-0) + benzyl 2-acetamido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside (112289-51-7) → N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide (206751-89-5)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

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

Reference yield: 89.0%

N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide (206751-89-5) → benzyl 2-acetamido-6-O-benzyl-2-deoxy-α-D-galactopyranoside (86319-58-6)

Guidance literature:

With acetic acid; In water; at 100 ℃; for 0.5h;

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

Reference yield:

N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide (206751-89-5) → (2R,3S,4R,5R,6R)-6-((2S,3R,4R,5R,6R)-3-Acetylamino-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid (206752-03-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / acetic acid / H₂O / 0.5 h / 100 °C

2: 1.) (+/-)-camphor-10-sulfonic acid, 2.) acetic acid / 1.) toluene, room temperature, 1 h, 2.) water, room temperature, 10 min

3: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 40 min, 2.) CH₂Cl₂, toluene, 0 deg C

4: 75 percent / thiourea, pyridine / ethanol / 24 h / 80 °C

5: 84 percent / triflic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: 1.) H₂O₂, lithium hydroxide, 2.) sodium hydroxide / 1.) THF, -5 deg C -> room temperature, 2.) THF, methanol, room temperature, 6 h

With pyridine; lithium hydroxide; sodium hydroxide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; dihydrogen peroxide; acetic acid; thiourea; In ethanol; dichloromethane; water;

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

upstream raw materials:

benzyl bromide

benzyl 2-acetamido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside

Downstream raw materials:

benzyl 2-acetamido-6-O-benzyl-2-deoxy-α-D-galactopyranoside

(2R,3S,4R,5R,6R)-6-((2S,3R,4R,5R,6R)-3-Acetylamino-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid

(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester