Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 803738-15-0
• Molecular Formula: C₅₉H₆₄O₁₂
• Molecular Weight: 965.15

Synonyms:Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-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: 71.0%

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) + pent-4-enyl 3,4-di-O-benzyl-α-D-mannopyranoside (803737-94-2) → Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (803738-15-0)

Guidance literature:

With N-iodo-succinimide; ytterbium(III) triflate; In dichloromethane; at 0 ℃; for 0.25h;

Reference yield:

benzyl bromide (100-39-0) → Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (803738-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; TBAI / dimethylformamide / 1 h

2: 71 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.25 h / 0 °C

With N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; sodium hydride; ytterbium(III) triflate; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (163039-18-7) → Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (803738-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; TBAI / dimethylformamide / 1 h

2: 71 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.25 h / 0 °C

With N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; sodium hydride; ytterbium(III) triflate; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

pent-4-enyl 3,4-di-O-benzyl-α-D-mannopyranoside

C₂₅H₃₂O₆COC₆H₄

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

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