[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Base Information

• Chemical Name: [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol
• CAS No.: 233744-16-6
• Molecular Formula: C₂₈H₃₁NO₈
• Molecular Weight: 509.556

Synonyms:[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Chemical Property of [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Chemical Property:

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Technology Process of [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

There total 1 articles about [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol 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: 96.0%

(2R,4aR,6S,7R,8S,8aR)-8-Benzyloxy-6-methoxy-7-(4-nitro-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (233744-16-6)

Guidance literature:

With dimethylamine borane; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃;

DOI:10.1055/s-1999-2779

Reference yield: 100.0%

[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (233744-16-6) → [(2R,3R,4S,5R,6S)-5-(4-Amino-benzyloxy)-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl]-methanol (233744-17-7)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol;

DOI:10.1055/s-2001-13392

Reference yield:

[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-methanol (233744-16-6) → Carbonic acid 2,2,2-trichloro-ethyl ester (2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-((2R,3R,4R,5R,6S)-3,4-bis-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / Zn-Cu; acetylacetone / tetrahydrofuran

2: 91 percent / tetrahydrofuran

3: 62 percent

With copper; acetylacetone; zinc; In tetrahydrofuran; 1: Reduction / 2: Acylation;

DOI:10.1055/s-1999-2779

Downstream raw materials:

[(2R,3R,4S,5R,6S)-5-(4-Amino-benzyloxy)-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl]-methanol

4-[4-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxymethyl)-phenylcarbamoyl]-butyric acid 4-(5-ethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylmethyl)-benzyl ester

4-[4-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxymethyl)-phenylcarbamoyl]-butyric acid

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