Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 200941-55-5
• Molecular Formula: C₆₄H₆₄O₁₄S
• Molecular Weight: 1089.27

Synonyms:Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl 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: 85.0%

Succinic acid (2R,4aS,6R,7S,8R,8aS)-7-benzoyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester → Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-55-5)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<163::AID-EJOC163>3.0.CO;2-I

Reference yield:

benzaldehyde (100-52-7) → Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnCl₂ / 4 h / 70 °C

2: 1.) 1-hyroxybenzotriazole; 2.) Et₃N / 1.) CH₂Cl₂, 30 min; CH₂Cl₂, room temp., 24 h

3: 64 percent / DCC, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

4: 85 percent / HCl, NaCNBH₃, mol. sieves (3 Angstroem) / tetrahydrofuran; diethyl ether / Ambient temperature

With hydrogenchloride; dmap; 3 A molecular sieve; sodium cyanoborohydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<163::AID-EJOC163>3.0.CO;2-I

Reference yield:

benzyl 4,6-O-benzylidene-α-L-glucopyranoside (200941-40-8) → Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hyroxybenzotriazole; 2.) Et₃N / 1.) CH₂Cl₂, 30 min; CH₂Cl₂, room temp., 24 h

2: 64 percent / DCC, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

3: 85 percent / HCl, NaCNBH₃, mol. sieves (3 Angstroem) / tetrahydrofuran; diethyl ether / Ambient temperature

With hydrogenchloride; dmap; 3 A molecular sieve; sodium cyanoborohydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199801)1998:1<163::AID-EJOC163>3.0.CO;2-I

upstream raw materials:

benzaldehyde

benzyl 4,6-O-benzylidene-α-L-glucopyranoside

benzyl 2-O-benzoyl-4,6-O-benzylidene-α-L-glucopyranoside

benzyl alcohol

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