(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol
• CAS No.: 180714-36-7
• Molecular Formula: C₄₇H₇₀O₈
• Molecular Weight: 763.068
• Mol file: 180714-36-7.mol

Synonyms:(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol

There total 4 articles about (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol 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: 100.0%

1-O-hexadecyl-2-O-methyl-3-O-(2'-O-acetyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)-sn-glycerol (180714-34-5) → (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol (180714-36-7)

Guidance literature:

With ammonia; In methanol; for 0.25h; Ambient temperature;

DOI:10.1021/jm960164j

Reference yield:

1-O-hexadecyl-2-O-methyl-sn-glycerol (96960-92-8,111188-59-1) → (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol (180714-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / molecular sieves 3A, TMSOTf / CH₂Cl₂ / 0.17 h / -78 °C

2: 100 percent / NH₃ (gas) / methanol / 0.25 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonia; In methanol; dichloromethane;

DOI:10.1021/jm960164j

Reference yield:

1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol (156737-65-4) → (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ol (180714-36-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT

2: 94 percent / aq. Ce(NO₃)4 / acetonitrile / 1 h / Ambient temperature

3: 76 percent / molecular sieves 3A, TMSOTf / CH₂Cl₂ / 0.17 h / -78 °C

4: 100 percent / NH₃ (gas) / methanol / 0.25 h / Ambient temperature

With cerium nitrate; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonia; sodium hydride; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm960164j

upstream raw materials:

1-O-hexadecyl-2-O-methyl-3-O-(2'-O-acetyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)-sn-glycerol

1-O-hexadecyl-2-O-methyl-sn-glycerol

1-O-hexadecyl-3-O-(p-methoxyphenyl)-sn-glycerol

1-O-Hexadecyl-2-O-methyl-3-O-(4-methoxyphenyl)-sn-glycerol

Downstream raw materials:

Dithiocarbonic acid O-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-yl] ester S-methyl ester

(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-5-methoxy-tetrahydro-pyran

(2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran