Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 204704-85-8
• Molecular Formula: C₃₈H₄₆O₁₂
• Molecular Weight: 694.776

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester 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: 79.0%

Acetic acid (4aR,6R,7R,8S,8aS)-8-acetoxy-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester (204704-85-8)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In diethyl ether; at 0 ℃; for 0.75h;

DOI:10.1080/00397919808006846

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-galacto-pyranoside (56119-28-9) → Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester (204704-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / NaH / dimethylformamide / 3 h

2: 80 percent / CuBr₂, Bu₄NBr, 4 Angstroem molecular sieves / 1,2-dichloro-ethane; dimethylformamide / 72 h / 24 °C

3: DDQ / CH₂Cl₂ / 12 h / Ambient temperature

4: 1.73 g / pyridine / 6 h / Ambient temperature

5: 79 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / diethyl ether / 0.75 h / 0 °C

With pyridine; hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(ll) bromide; In diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1080/00397919808006846

Reference yield:

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (69850-47-1) → Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester (204704-85-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / CuBr₂, Bu₄NBr, 4 Angstroem molecular sieves / 1,2-dichloro-ethane; dimethylformamide / 72 h / 24 °C

2: DDQ / CH₂Cl₂ / 12 h / Ambient temperature

3: 1.73 g / pyridine / 6 h / Ambient temperature

4: 79 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / diethyl ether / 0.75 h / 0 °C

With pyridine; hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(ll) bromide; In diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1080/00397919808006846

upstream raw materials:

ethyl 4,6-O-benzylidene-1-thio-β-D-galacto-pyranoside

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

Downstream raw materials:

C₇₂H₈₀O₁₇

(2R,3R,4R,5R,6R)-6-Benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol

C₇₂H₈₀O₁₇

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