(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Base Information

• Chemical Name: (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS No.: 870101-07-8
• Molecular Formula: C₃₄H₄₂O₇Si
• Molecular Weight: 590.789

Synonyms:(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Chemical Property of (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Chemical Property:

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Technology Process of (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

There total 1 articles about (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 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:

(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) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (870101-07-8)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 24h;

DOI:10.1021/ja00110a010

Reference yield: 88.0%

(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (870101-07-8) → 6-O-tert-butyldiphenylsilyl-2-O-benzoyl-α-D-mannopyranosyl fluoride (1187620-65-0)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at -40 ℃; Inert atmosphere;

DOI:10.1021/ol901630d

Reference yield: 60.0%

(3aS,5R,6S,7S,7aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (870101-07-8) + 1,2,3,4-tetra-O-methyl-α-D-glucopyranose (4153-24-6) → benzoic acid 6-(tert-butyl-diphenyl-silanyloxymethyl)-4,5-dihydroxy-2-(3,4,5,6-tetramethoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (870101-08-9)

Guidance literature:

With N-Bromosuccinimide; boron trifluoride diethyl etherate;

DOI:10.1039/b507468a

upstream raw materials:

(3aS,5R,6S,7S,7aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

C₅₂H₆₆O₁₈Si

benzoic acid 6-(tert-butyl-diphenyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-3,5-dihydroxy-6-(3,4,5,6-tetramethoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yloxy]-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

C₆₅H₈₀O₂₄Si

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