(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:284663-21-4
Molecular Formula:C₅₉H₆₄O₁₁
Molecular Weight:949.151
Hs Code.:

(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Synonyms:(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 6 articles about (2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 97.0%

: 100-39-0
benzyl bromide

: 284663-03-2
Pent-4-enyl 3'-O-benzyl-4',6'-O-benzylidenyl-β-D-lactoside

: 284663-21-4
(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With tetraethylammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 14h;
DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

Reference yield:

: 153228-87-6
n-pentenyl (β-D-galactopyranosyl)-(1<*>4)-β-D-glucopyranoside

: 284663-21-4
(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂SnO / benzene / 15 h / Heating

1.2: 54 percent / Bu₄NI / benzene / 3.5 h / Heating

2.1: 72 percent / CSA / acetonitrile; dimethylformamide / 16 h / 20 °C

3.1: 97 percent / Et₄NI; NaH / dimethylformamide / 14 h / 0 - 20 °C

With camphor-10-sulfonic acid; tetraethylammonium iodide; sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Cyclization / 1.2: Etherification / 2.1: Cyclization / 3.1: Etherification;
DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

Reference yield:

: 4753-07-5
2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

: 284663-21-4
(2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / Ag₂CO₃; molecular sieves 4 Angstroem; I₂ / CH₂Cl₂ / 16 h / 20 °C

2.1: 100 percent / NaOMe / methanol / 16 h / 20 °C

3.1: Bu₂SnO / benzene / 15 h / Heating

3.2: 54 percent / Bu₄NI / benzene / 3.5 h / Heating

4.1: 72 percent / CSA / acetonitrile; dimethylformamide / 16 h / 20 °C

5.1: 97 percent / Et₄NI; NaH / dimethylformamide / 14 h / 0 - 20 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; tetraethylammonium iodide; iodine; sodium methylate; sodium hydride; di(n-butyl)tin oxide; silver carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Glycosidation / 2.1: Deacetylation / 3.1: Cyclization / 3.2: Etherification / 4.1: Cyclization / 5.1: Etherification;
DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K