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

Base Information

• Chemical Name: Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 200941-45-3
• Molecular Formula: C₆₄H₆₄O₁₄S
• Molecular Weight: 1089.27

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Useful:

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

There total 10 articles about Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-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: 76.0%

Succinic acid (2S,4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester → Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-45-3)

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:

benzyl bromide (100-39-0) → Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-45-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / 1.) NaH / dimethylformamide / 3 h / Ambient temperature; 1.) 0 deg C

2: 78 percent / p-toluenesulfonic acid / CHCl₃; methanol / 0.67 h / Ambient temperature

3: 92 percent / DMAP, pyridine / 24 h / Ambient temperature

4: 63 percent / DCC, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

5: 76 percent / HCl, NaCNBH₃, mol. sieves (3 Angstroem) / tetrahydrofuran; diethyl ether / Ambient temperature

With pyridine; hydrogenchloride; dmap; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;

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

Reference yield:

1,2,3,4,6‐pentaacetyl L‐mannopyranoside (115792-70-6) → Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (200941-45-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 69 percent / boron trifluoride diethyl ether / CH₂Cl₂ / 18 h / Ambient temperature

2: 1M NaOMe / methanol / 3 h / Ambient temperature

3: 80 percent / pyridine / 24 h / Ambient temperature

4: 85 percent / 1.) NaH / dimethylformamide / 3 h / Ambient temperature; 1.) 0 deg C

5: 78 percent / p-toluenesulfonic acid / CHCl₃; methanol / 0.67 h / Ambient temperature

6: 92 percent / DMAP, pyridine / 24 h / Ambient temperature

7: 63 percent / DCC, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

8: 76 percent / HCl, NaCNBH₃, mol. sieves (3 Angstroem) / tetrahydrofuran; diethyl ether / Ambient temperature

With pyridine; hydrogenchloride; dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;

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

upstream raw materials:

benzyl bromide

1,2,3,4,6‐pentaacetyl L‐mannopyranoside

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-mannopyranoside

phenyl 6-O-trityl-1-thio-α-L-mannopyranoside

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