(2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol
• CAS No.: 211239-18-8
• Molecular Formula: C₃₄H₄₅NO₉
• Molecular Weight: 611.733

Synonyms:(2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol

Chemical Property of (2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol

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Technology Process of (2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol

There total 1 articles about (2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-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: 6.0%

(1S,2S,3S,4R)-1-amino-5-(hydroxymethyl)-2,3:4,6-di-O-isopropylidene-5-cyclohexene-2,3,4-triol (90025-02-8) + methyl 2,3-anhydro-4,6-di-O-benzyl-α-D-mannopyranoside (146195-58-6) → (2S,3S,4S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methoxy-4-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-3-ol (211239-06-4) + (2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol (211239-18-8)

Guidance literature:

In isopropyl alcohol; at 120 ℃; for 120h;

DOI:10.1016/S0008-6215(98)00045-7

Reference yield: 96.0%

(2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol (211239-18-8) → (1S,2S,3R,6S)-6-((2S,3R,4R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol (211239-26-8)

Guidance literature:

With acetic acid; at 60 ℃; for 3h;

DOI:10.1016/S0008-6215(98)00045-7

Reference yield:

(2R,3S,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-methoxy-5-((3aS,4S,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-tetrahydro-pyran-4-ol (211239-18-8) → (1S,2S,3R,6S)-6-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol (211237-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / aq 80percent acetic acid / 3 h / 60 °C

2: 78 percent / Na, NH₃(l) / tetrahydrofuran / 15 h / -75 °C

With ammonia; sodium; acetic acid; In tetrahydrofuran;

DOI:10.1016/S0008-6215(98)00045-7

upstream raw materials:

(1S,2S,3S,4R)-1-amino-5-(hydroxymethyl)-2,3:4,6-di-O-isopropylidene-5-cyclohexene-2,3,4-triol

methyl 2,3-anhydro-4,6-di-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

(1S,2S,3R,6S)-6-((2S,3R,4R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol

(1S,2S,3R,6S)-6-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol

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