(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

Base Information

• Chemical Name: (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
• CAS No.: 507485-55-4
• Molecular Formula: C₄₁H₅₂O₁₁
• Molecular Weight: 720.857

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

(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 → (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 (507485-55-4)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran;

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

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → (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 (507485-55-4)

Guidance literature:

Multi-step reaction with 4 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

With 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) → (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 (507485-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

2: lithium triethylborohydride / tetrahydrofuran

With 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

upstream raw materials:

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

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

Downstream raw materials:

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

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-O-acetyl-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

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