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

Base Information

• Chemical Name: (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-ol
• CAS No.: 127924-52-1
• Molecular Formula: C₆₄H₆₆O₁₁
• Molecular Weight: 1011.22

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-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:

alpha-D-glucopyranose (492-62-6) → (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-ol (127924-52-1,127995-76-0)

Guidance literature:

Multi-step reaction with 5 steps

2: 2.) thexylborane, H₂O₂, NaOH / 1.) THF, o deg C to room temp.; 2.) THF

3: 98 percent / ClCOCOC, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 to -48 deg C

4: Ph₃P, Zn / CH₂Cl₂ / Ambient temperature

5: 1.) n-BuLi / 1.) THF, -78 to -40 deg C

With sodium hydroxide; n-butyllithium; thexylborane; dihydrogen peroxide; triethylamine; triphenylphosphine; zinc; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)76178-8

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-ol (127924-52-1,127995-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, ClCOCOCl / dimethylsulfoxide; CH₂Cl₂ / -78 deg C

2: 1.) n-BuLi / 1.) THF, -78 to -40 deg C

With n-butyllithium; oxalyl dichloride; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)76178-8

Reference yield:

benzyl bromide (100-39-0) → (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-ol (127924-52-1,127995-76-0)

Guidance literature:

Multi-step reaction with 5 steps

2: 2.) thexylborane, H₂O₂, NaOH / 1.) THF, o deg C to room temp.; 2.) THF

3: 98 percent / ClCOCOC, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 to -48 deg C

4: Ph₃P, Zn / CH₂Cl₂ / Ambient temperature

5: 1.) n-BuLi / 1.) THF, -78 to -40 deg C

With sodium hydroxide; n-butyllithium; thexylborane; dihydrogen peroxide; triethylamine; triphenylphosphine; zinc; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)76178-8

upstream raw materials:

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

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

alpha-D-glucopyranose

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

C₆₄H₆₆O₁₀

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