(2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol
• CAS No.: 138061-52-6
• Molecular Formula: C₅₀H₅₈O₉S
• Molecular Weight: 835.071

Synonyms:

Chemical Property of (2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol

There total 16 articles about (2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-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:

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (365418-30-0) → (2R,4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol (138061-52-6,138230-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; dibutyl ether / 0.33 h / Ambient temperature

2: Swern oxidation

3: 1.) lithium hexamethyldisilazane / 1.) THF, hexanes, -78 deg C, 20 min, 2.) 10 min

4: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 30 min, 2.) methylene chloride, -15 deg C

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; dibutyl ether;

DOI:10.1021/jo00028a019

Reference yield:

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanal)-α-D-glucopyranoside (365418-30-0) → (2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol (138061-52-6,138230-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; dibutyl ether / 0.33 h / Ambient temperature

2: Swern oxidation

3: 1.) lithium hexamethyldisilazane / 1.) THF, hexanes, -78 deg C, 20 min, 2.) 10 min

4: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 30 min, 2.) methylene chloride, -15 deg C

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; dibutyl ether;

DOI:10.1021/jo00028a019

Reference yield:

2-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-48-0) → (2R,4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol (138061-52-6,138230-68-9)

Guidance literature:

Multi-step reaction with 5 steps

1: Swern oxidation

2: tetrahydrofuran; dibutyl ether / 0.33 h / Ambient temperature

3: Swern oxidation

4: 1.) lithium hexamethyldisilazane / 1.) THF, hexanes, -78 deg C, 20 min, 2.) 10 min

5: 1.) TBAF*3H₂O, 2.) BF₃*OEt₂ / 1.) THF, r.t., 30 min, 2.) methylene chloride, -15 deg C

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; dibutyl ether;

DOI:10.1021/jo00028a019

upstream raw materials:

methylthiol

(4S,5R,6R)-5,7-Bis-benzyloxy-1-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-heptan-2-one

1,3-O-Dibenzyl-2-O-(tert-butyldimethylsilyl)threitol

(2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

Downstream raw materials:

(2R,3R,4S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-ol

(2R,3S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-one

(2R,3S,5S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[hydroxy-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-methyl]-tetrahydro-pyran-4-one

(2R,3S,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-[hydroxy-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-methyl]-tetrahydro-pyran-4-one

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