(2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine
• CAS No.: 186820-74-6
• Molecular Formula: C₅₆H₆₀O₁₀
• Molecular Weight: 893.086

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

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

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

There total 6 articles about (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[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: 92.0%

benzyl bromide (100-39-0) + (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol (186820-68-8) → (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine (186820-74-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (19488-49-4) → (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine (186820-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH, 15-crown-5 ether / 1) DMF, RT, 1 h, 2) DMF, 70 deg C, 3 h

2: 74 percent / DMSO, Ac₂O / 4 h / Ambient temperature

3: 58 percent / DBU / toluene / 0.33 h / 80 °C

4: 50 percent / NaBH₄, CeCl₃*7H₂O / methanol; CH₂Cl₂ / 0.5 h / Ambient temperature

5: 92 percent / NaH / dimethylformamide / 24 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose (142789-96-6) → (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxine (186820-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH, 15-crown-5 ether / 1) DMF, RT, 1 h, 2) DMF, 70 deg C, 3 h

2: 74 percent / DMSO, Ac₂O / 4 h / Ambient temperature

3: 58 percent / DBU / toluene / 0.33 h / 80 °C

4: 50 percent / NaBH₄, CeCl₃*7H₂O / methanol; CH₂Cl₂ / 0.5 h / Ambient temperature

5: 92 percent / NaH / dimethylformamide / 24 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

upstream raw materials:

benzyl bromide

(2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-benzo[1,3]dioxin-7-ol

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

1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose

Downstream raw materials:

(1R,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

(2R,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanone

(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

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