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

Base Information

• Chemical Name: (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran
• CAS No.: 180714-42-5
• Molecular Formula: C₄₇H₇₀O₇
• Molecular Weight: 747.069
• Mol file: 180714-42-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran 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: 97.0%

3-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran-3-ylsulfanyl]-4-methyl-pent-3-en-2-one → (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran (180714-42-5)

Guidance literature:

With nickel; In benzene; for 1h; Ambient temperature;

DOI:10.1021/jo971934h

Reference yield: 92.0%

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 (180714-40-3) → (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran (180714-42-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1021/jm960164j

Reference yield:

1-O-hexadecyl-2-O-methyl-sn-glycerol (96960-92-8,111188-59-1) → (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-3-hexadecyloxy-2-methoxy-propoxy)-tetrahydro-pyran (180714-42-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / triflic acid, 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -20 °C

2: 97 percent / Raney nickel / benzene / 1 h / Ambient temperature

With trifluorormethanesulfonic acid; 3 A molecular sieve; nickel; In dichloromethane; benzene;

DOI:10.1021/jo971934h

upstream 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

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

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose

(4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene