Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester
• CAS No.: 507485-56-5
• Molecular Formula: C₄₃H₅₄O₁₂
• Molecular Weight: 762.895

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester

Chemical Property:

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Safty Information:

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Technology Process of Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester

There total 5 articles about Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-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:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester (507485-56-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂

2.1: sodium / methanol / 8 h / 20 °C

2.2: p-toluenesulfonic acid / acetone / 20 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

4.1: lithium triethylborohydride / tetrahydrofuran

5.1: pyridine / 20 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

Reference yield:

methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside (507485-53-2) → Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester (507485-56-5)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

2: lithium triethylborohydride / tetrahydrofuran

3: pyridine / 20 °C

With pyridine; oxalyl dichloride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

Reference yield:

(2R,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-tetrahydro-1,5,7-trioxa-benzocyclohepten-3-one → Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester (507485-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium triethylborohydride / tetrahydrofuran

2: pyridine / 20 °C

With pyridine; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

upstream raw materials:

acetic anhydride

(2R,3S,4R,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-ol

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

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