(S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol

Base Information

• Chemical Name: (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol
• CAS No.: 136337-42-3
• Molecular Formula: C₆₉H₇₂O₁₂
• Molecular Weight: 1093.32

Synonyms:(S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol

Chemical Property of (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol

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Technology Process of (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol

There total 3 articles about (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol 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%

Benzyl 6-O-(7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranose (136337-36-5) → (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol (136337-42-3)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 40 - 50 ℃; for 24h;

DOI:10.1016/0008-6215(91)84032-A

Reference yield:

benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside (59935-49-8) → (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol (136337-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51.3 percent / 4A molecular sieves, p-TsOH / CH₂Cl₂ / 24 h / Ambient temperature

2: 76 percent / p-TsOH, water / methanol; tetrahydrofuran / 24 h / 40 - 50 °C

With 4 A molecular sieve; water; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0008-6215(91)84032-A

Reference yield:

7-O-Allyl-2,3,4,6-tetra-O-benzyl-1-O-trichloroacetimidoyl-L-glycero-α-D-manno-heptopyranose (111549-82-7) → (S)-2-Benzyloxy-2-[(2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-ethanol (136337-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51.3 percent / 4A molecular sieves, p-TsOH / CH₂Cl₂ / 24 h / Ambient temperature

2: 76 percent / p-TsOH, water / methanol; tetrahydrofuran / 24 h / 40 - 50 °C

With 4 A molecular sieve; water; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0008-6215(91)84032-A

upstream raw materials:

Benzyl 6-O-(7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranose

benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

7-O-Allyl-2,3,4,6-tetra-O-benzyl-1-O-trichloroacetimidoyl-L-glycero-α-D-manno-heptopyranose

Downstream raw materials:

6-O-L-Glycero-α-D-manno-heptopyranosyl-α-D-glucopyranose

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